Dimethylformamide → Methyl 3-[3-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoate

HRID 2165203Notes

Reaction equation

HRID 2165203 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:23](=[O:24])[C:22]4=[CH:25][S:26][CH:27]=[C:21]4[NH:20][C:19]3=[O:28])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:31]([O:35][CH3:36])(=[O:34])[CH:32]=[CH2:33].CN(C=O)C>CCOCC.CCCCCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]3[C:23](=[O:24])[C:22]4=[CH:25][S:26][CH:27]=[C:21]4[N:20]([CH2:33][CH2:32][C:31]([O:35][CH3:36])=[O:34])[C:19]3=[O:28])[CH2:10][CH2:9]2)=[O:7])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 145004063-[4-[4-(4-Fluorobenzoyl)piperidin-1-yl]-butyl]thieno[3,4-d]pyrimidine-2,4-dione

Product 1

HCID 15070686Methyl 3-[3-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoateYield 64.6%

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

The title compound was prepared by starting with 3-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]thieno[3,4-d]pyrimidine-2,4-dione. This material (2.91 g, 6.8 mmol) was reacted with methyl acrylate as described in Example 1 using DMF as the solvent to produce 2.26 g (64.6%) of methyl 3-[3-[4-[4-(4-fluorobenzoyl)piperidin-1-yl]butyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoate as a creamed-colored solid after trituration with ether/hexane, mp 102.5°-103.5° C.

Sources & evidence

ORD record
ord-d49e4cca2694431a942810253799342d
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

Loading…