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molecular formula C31H49O2P B580627 tBuBrettPhos CAS No. 1160861-53-9

tBuBrettPhos

Cat. No. B580627
M. Wt: 484.705
InChI Key: REWLCYPYZCHYSS-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US09434698B2

Procedure details

Tris(dibenzylideneacetone)dipalladium(0) (0.0071 g, 7.71 μmol), di-tert-butyl(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine (0.0089 g, 19.0 μmol) and milled potassium phosphate tribasic (0.360 g, 1.696 mmol) were charged to a 40-mL reaction vial inside an inert atmosphere glove box. 2-Methyltetrahydrofuran (4 mL) was added, and the closed vial and its contents were heated to 80° C. with magnetic stirring for 30 minutes. The reaction mixture was cooled down to room temperature. 6-(3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate (1.0 g, 1.542 mmol, Example 3-4, compound (5c)), methanesulfonamide (0.176 g, 1.850 mmol) and ethyl acetate (8 mL) were added to the 40-mL reaction vial. The temperature of the closed vial and its contents was raised to 90° C. and stirred for 20 hours. HPLC analysis of the reaction mixture showed that the product was formed in 95 area % at 210 nm.
Quantity
4 mL
Type
reactant
Reaction Step One
Name
6-(3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate
Quantity
1 g
Type
reactant
Reaction Step Two
Name
compound ( 5c )
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
Quantity
0.176 g
Type
reactant
Reaction Step Two
Quantity
8 mL
Type
solvent
Reaction Step Two
Quantity
0.0089 g
Type
reactant
Reaction Step Three
Name
potassium phosphate tribasic
Quantity
0.36 g
Type
reactant
Reaction Step Three
Quantity
0.0071 g
Type
catalyst
Reaction Step Three

Identifiers

REACTION_CXSMILES
C(P(C(C)(C)C)C1C(OC)=CC=C(OC)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC1CCCO1.FC(F)(F)C(F)(S(O[C:60]1[CH:69]=[CH:68][C:67]2[C:62](=[CH:63][CH:64]=[C:65]([C:70]3[CH:75]=[C:74]([N:76]4[CH:81]=[CH:80][C:79](=[O:82])[NH:78][C:77]4=[O:83])[CH:73]=[C:72]([C:84]([CH3:87])([CH3:86])[CH3:85])[C:71]=3[O:88][CH3:89])[CH:66]=2)[CH:61]=1)(=O)=O)C(F)(F)F.[CH3:93][S:94]([NH2:97])(=[O:96])=[O:95]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[C:84]([C:72]1[C:71]([O:88][CH3:89])=[C:70]([C:65]2[CH:66]=[C:67]3[C:62](=[CH:63][CH:64]=2)[CH:61]=[C:60]([NH:97][S:94]([CH3:93])(=[O:96])=[O:95])[CH:69]=[CH:68]3)[CH:75]=[C:74]([N:76]2[CH:81]=[CH:80][C:79](=[O:82])[NH:78][C:77]2=[O:83])[CH:73]=1)([CH3:86])([CH3:87])[CH3:85] |f:1.2.3.4,8.9.10.11.12|

Inputs

Step One
Name
Quantity
4 mL
Type
reactant
Smiles
CC1OCCC1
Step Two
Name
6-(3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl 1,1,1,2,3,3,3-heptafluoropropane-2-sulfonate
Quantity
1 g
Type
reactant
Smiles
FC(C(C(F)(F)F)(S(=O)(=O)OC1=CC2=CC=C(C=C2C=C1)C1=C(C(=CC(=C1)N1C(NC(C=C1)=O)=O)C(C)(C)C)OC)F)(F)F
Name
compound ( 5c )
Quantity
0 (± 1) mol
Type
reactant
Smiles
FC(C(C(F)(F)F)(S(=O)(=O)OC1=CC2=CC=C(C=C2C=C1)C1=C(C(=CC(=C1)N1C(NC(C=C1)=O)=O)C(C)(C)C)OC)F)(F)F
Name
Quantity
0.176 g
Type
reactant
Smiles
CS(=O)(=O)N
Name
Quantity
8 mL
Type
solvent
Smiles
C(C)(=O)OCC
Step Three
Name
Quantity
0.0089 g
Type
reactant
Smiles
C(C)(C)(C)P(C1=C(C(=CC=C1OC)OC)C1=C(C=C(C=C1C(C)C)C(C)C)C(C)C)C(C)(C)C
Name
potassium phosphate tribasic
Quantity
0.36 g
Type
reactant
Smiles
[O-]P(=O)([O-])[O-].[K+].[K+].[K+]
Name
Quantity
0.0071 g
Type
catalyst
Smiles
C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
80 °C
Stirring
Type
CUSTOM
Details
with magnetic stirring for 30 minutes
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
were charged to a 40-mL reaction vial inside an inert atmosphere glove box
TEMPERATURE
Type
TEMPERATURE
Details
The reaction mixture was cooled down to room temperature
TEMPERATURE
Type
TEMPERATURE
Details
The temperature of the closed vial and its contents was raised to 90° C.
STIRRING
Type
STIRRING
Details
stirred for 20 hours
Duration
20 h
CUSTOM
Type
CUSTOM
Details
was formed in 95 area % at 210 nm

Outcomes

Product
Details
Reaction Time
30 min
Name
Type
Smiles
C(C)(C)(C)C=1C(=C(C=C(C1)N1C(NC(C=C1)=O)=O)C=1C=C2C=CC(=CC2=CC1)NS(=O)(=O)C)OC

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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