Dimethylformamide → Methyl 3-[3-[5-[4-(3-trifluoromethylphenyl)piperazin-1-yl]pentyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoate

HRID 2165206Notes

Reaction equation

HRID 2165206 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([N: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:6]=[CH:7][CH:8]=1.CN([CH:36]=[O:37])C>>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:10][CH2:11][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]([CH2:23][CH2:24][C:25]([O:37][CH3:36])=[O:26])[C:21]3=[O:30])[CH2:13][CH2:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 150706883-[5-[4-(3-Trifluoromethylphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione

Product 1

HCID 15070689Methyl 3-[3-[5-[4-(3-trifluoromethylphenyl)piperazin-1-yl]pentyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoateYield 41%

Procedure

The title compound was produced following the procedure of Example 1 using 12.0 g (26 mmol) of 3-[5-[4-(3-trifluoromethylphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione in DMF at 50° C. for 24 hours to produce methyl 3-[3-[5-[4-(3-trifluoromethylphenyl)piperazin-1-yl]pentyl]-2,4-dioxothieno[3,4-d]pyrimidin-1-yl]propanoate in 41% yield (5.78 g) after recrystallization from ether/hexane, mp 99.5°-101° C.

Workup

  1. customat 50° C.
  2. customfor 24 hours

Sources & evidence

ORD record
ord-08cc2b49103b4b28ae2389ec4d2214ab
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

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