Acetyl chloride → N-{4-[2-(1-benzothien-3-ylmethyl)-7-isobutyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-5-methyl-1,3-thiazol-2-yl}acetamide

HRID 1181790Notes

Reaction equation

HRID 1181790 reaction equation
Cl.[NH2:2][C:3]1[S:4][C:5]([CH3:34])=[C:6]([C:8]2[N:9]([CH2:24][C:25]3[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[S:27][CH:26]=3)[N:10]=[C:11]3[C:16]=2[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[O:19])[N:12]3[CH2:20][CH:21]([CH3:23])[CH3:22])[N:7]=1.[C:35](Cl)(=[O:37])[CH3:36].C(=O)([O-])[O-].[K+].[K+]>C(N(CC)CC)C>[S:27]1[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:25]([CH2:24][N:9]2[C:8]([C:6]3[N:7]=[C:3]([NH:2][C:35](=[O:37])[CH3:36])[S:4][C:5]=3[CH3:34])=[C:16]3[C:11]([N:12]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13](=[O:19])[N:14]([CH3:18])[C:15]3=[O:17])=[N:10]2)=[CH:26]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 865954303-(2-amino-5-methyl-1,3-thiazol-4-yl)-2-(1-benzothien-3-ylmethyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione hydrochloride

Product 1

HCID 58981114N-{4-[2-(1-benzothien-3-ylmethyl)-7-isobutyl-5-methyl-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]-5-methyl-1,3-thiazol-2-yl}acetamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-(2-amino-5-methyl-1,3-thiazol-4-yl)-2-(1-benzothien-3-ylmethyl)-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione hydrochloride was reacted with excess acetyl chloride using triethylamine as a base. The resulting bis acetylated product is treated with potassium carbonate to give the title compound. Mass: 523.22 (M+H).

Sources & evidence

ORD record
ord-ae002f5f98bf446a93a3ab9d4960ffb3
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

Loading…