Toluene → HCID 45138979, compound

HRID 2278731Notes

Reaction equation

HRID 2278731 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:15]([NH:17][CH2:18][C:19]2[CH:20]=[N:21][C:22]([CH3:25])=[N:23][CH:24]=2)=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:31]1[N:36]=[CH:35][CH:34]=[CH:33][N:32]=1)CCC.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][C:22]1[N:21]=[CH:20][C:19]([CH2:18][NH:17][C:15]([C:4]2[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)[CH:7]=[C:2]([C:31]3[N:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[CH:3]=2)=[O:16])=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 27632512-(Tributylstannyl)pyrimidineHCID 58449346HCID 58449346, compound

Product 1

HCID 45138979HCID 45138979, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-4′-methyl-N-((2-methylpyrimidin-5-yl)methyl)biphenyl-3-carboxamide (100 mg, 0.0002 mol), 2-(tributylstannyl)pyrimidine (0.1 g, 0.0003 mol), tetrakis(triphenylphosphine)palladium(0) (6 mg, 0.000005 mol) and toluene (1 mL, 0.009 mol) was heated in the microwave at 120° C. for 1 hour. LC/MS showed the desired product, LC/MS m/e=396.3. The mixture was cooled to room temperature and the reaction mixture filtered over celite and solvent removed under reduced pressure. The residue was purified by reverse phase prep HPLC to get the product as white solid.

Sources & evidence

ORD record
ord-301af4bccb214995919578bc3314a836
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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