Methyl Acrylate → Methyl 3-[3-[5-[4-[bis(4-fluorophenyl)methylene]piperidin-1-yl]pentyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoate

HRID 2165207Notes

Reaction equation

HRID 2165207 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:25](=[O:26])[C:24]4=[CH:27][S:28][CH:29]=[C:23]4[NH:22][C:21]3=[O:30])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[C:38]([O:42][CH3:43])(=[O:41])[CH:39]=[CH2:40]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)=[C:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:25](=[O:26])[C:24]4=[CH:27][S:28][CH:29]=[C:23]4[N:22]([CH2:40][CH2:39][C:38]([O:42][CH3:43])=[O:41])[C:21]3=[O:30])[CH2:11][CH2:10]2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7294Methyl AcrylateHCID 145004073-[5-[4-(Bis(4-fluorophenyl)methylene]piperidin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione

Product 1

HCID 15070687Methyl 3-[3-[5-[4-[bis(4-fluorophenyl)methylene]piperidin-1-yl]pentyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoateYield 57%

Procedure

The title compound was prepared by starting with 3-[5-[4-(bis(4-fluorophenyl)methylene]piperidin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione. This material (11.0 g, 21 mmol) was reacted with methyl acrylate as described in Example 1 to produce 8.06 g (57%) of methyl 3-[3-[5-[4-[bis(4-fluorophenyl)methylene]piperidin-1-yl]pentyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoate as a yellow oil. A portion of this material was converted to its crystalline oxalate salt by dissolving in acetone and treating with 1.1 equivalents of oxalic acid. There was obtained a cream-colored solid, mp 129°-136° C.

Sources & evidence

ORD record
ord-c4b860856e0d419ba317327a72c717ce
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

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