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

HRID 2165201Notes

Reaction equation

HRID 2165201 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]3[C:21](=[O:22])[C:20]4=[CH:23][S:24][CH:25]=[C:19]4[NH:18][C:17]3=[O:26])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:29]([O:33][CH3:34])(=[O:32])[CH:30]=[CH2:31]>>[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][N:16]3[C:21](=[O:22])[C:20]4=[CH:23][S:24][CH:25]=[C:19]4[N:18]([CH2:31][CH2:30][C:29]([O:33][CH3:34])=[O:32])[C:17]3=[O:26])[CH2:10][CH2:9]2)=[O:7])=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 7294Methyl AcrylateHCID 145003983-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione

Product 1

HCID 15070691Methyl 3-[3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoateYield 59.8%

Procedure

The title compound was prepared by starting with 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione. This material (9.0 g, 22.4 mmol) was reacted with methyl acrylate as described in Example 1 to produce 6.54 g (59.8%) of methyl 3-[3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoate as an orange oil after chromatography. A portion of this material was crystallized from CH2Cl2 /hexane to afford a peach-colored solid, mp 122°-123° C.

Sources & evidence

ORD record
ord-3087925c94314f42ae2e94966554cf12
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

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