Acetic Anhydride → N-[6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-yl]acetamide

HRID 32537Notes

Reaction equation

HRID 32537 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:16][C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH2:15])[C:9]=3[CH:8]=2)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[CH:3]1.[CH3:23][C:24](N(C)C)=[O:25].CCN(C(C)C)C(C)C.C(OC(=O)C)(=O)C>O>[CH3:1][N:2]1[C:6]([C:7]2[S:16][C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH:15][C:24](=[O:25])[CH3:23])[C:9]=3[CH:8]=2)=[C:5]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:4]=[CH:3]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 31374DimethylacetamideHCID 81531DiisopropylethylamineHCID 104704756-(1-methyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 10450481N-[6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidin-4-yl]acetamideYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)thieno[2,3-d]pyrimidine-4-amine (Example 8) (29 mg), DMA (2 mL), DIPEA (0.05 mL) and acetic anhydride (0.01 mL) were heated at 82° C. for 1 day. The reaction mixture was cooled to ambient temperature, water (2 mL) added and then preparative RPHPLC (eluting with a gradient of MeCN and water containing 0.1% TFA) afforded the title compound as a colourless solid (25 mg, 76%);

Workup

  1. washpreparative RPHPLC (eluting with a gradient of MeCN and water containing 0.1% TFA)

Sources & evidence

ORD record
ord-706dc7a9d23b429c8f5e056bdd834f38
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

Loading…