Carbon Dioxide → 1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]thieno[2,3-d]pyrimidine-5-carboxylic acid

HRID 900751노트

반응식

HRID 900751 반응식
Br[C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26].[C:29](=[O:31])=[O:30]>C1COCC1>[CH3:12][N:8]1[C:9](=[O:11])[C:10]2[C:2]([C:29]([OH:31])=[O:30])=[C:3]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])[S:4][C:5]=2[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7]1=[O:13]

참가 물질

4

반응물 2

HCID 280Carbon DioxideHCID 114429025-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 52825261,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-[[2-(trifluoromethyl)phenyl]methyl]thieno[2,3-d]pyrimidine-5-carboxylic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 5-bromo-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (WO 0183489) in THF (60 ml) was added isopropylmagnesiumcholride (2M solution in THF, 3.35 ml) dropwise at 0° C. under nitrogen. After 5 min the mixture was treated with a stream of carbon dioxide for 10 min. The reaction mixture was quenched with water, acidified 2N HCl and extracted into ethyl acetate (×3). The combined organic extracts were washed with dilute HCl, brine, dried (MgSO4) and concentrated in vacuo to give the subtitle compound as a yellow solid (2.48 g).

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted into ethyl acetate (×3)
  3. washThe combined organic extracts were washed with dilute HCl, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5b3beb52adbd4baea0195f59708d18bb
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361660B2

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