Sodium Carbonate → 2-(1-Methyl-2,4-diphenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine

HRID 32545Notes

Reaction equation

Br[C:2]1[N:3]([CH3:24])[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([S:22][CH3:23])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>COCCOC.O.C1(P([Pd-4](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)C=CC=CC=1>[CH3:24][N:3]1[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([S:22][CH3:23])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=[C:2]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-(2-bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)-[1,3]thiazolo[5,4-d]pyrimidine (Intermediate 37) (50 mg), tetrakis(triphenylphosphino)palladium(0) (28 mg), sodium carbonate (33 mg) and phenylboronic acid (14 mg) in DME (2 mL) and water (1 mL) was heated at 90° C. for 2 hours. After cooling to ambient temperature and extraction into DCM (3×5 mL), the combined organics were dried, filtered and the solvent evaporated in vacuo to give a brown oil. Purification by flash chromatography on silica eluting with EtOAC:hexane (1:9) gave the title compound as a yellow solid (25 mg, 50%);

Workup

temperatureAfter cooling to ambient temperature
extractionextraction into DCM (3×5 mL)
customthe combined organics were dried
filtrationfiltered
customthe solvent evaporated in vacuo
customto give a brown oil
customPurification by flash chromatography on silica eluting with EtOAC

Sources & evidence

ORD record: ord-56afae63d6544ed7899836d3083b2e3b
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427616B2

Reaction notes

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