Water → 3-(2-(3,5-Bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 1094711노트

반응식

HRID 1094711 반응식
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:31])[CH2:15][N:16]2[C:21](=[O:22])[C:20]3[C:23]([CH3:30])=[C:24]([C:26]([O:28]C)=[O:27])[S:25][C:19]=3[N:18]=[CH:17]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O.O.[OH-].[Li+]>C1COCC1.CO>[F:32][C:2]([F:1])([F:33])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:31])[CH2:15][N:16]2[C:21](=[O:22])[C:20]3[C:23]([CH3:30])=[C:24]([C:26]([OH:28])=[O:27])[S:25][C:19]=3[N:18]=[CH:17]2)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59842865Methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

생성물 1

HCID 453959523-(2-(3,5-Bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid수율 59%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate, (3.3 g, 6.75 mmol) in THF (30 mL), MeOH (10 mL), and H2O (10 mL) was added lithium hydroxide monohydrate (1.42 g, 33.8 mmol). The reaction mixture was then stirred at RT overnight. The reaction mixture was concentrated, diluted with H2O (30 mL) and washed with DCM (2×30 mL). The aqueous layer was acidified (pH˜2) with 1M HCl and the resultant precipitate was filtered and dried to give 1.9 g of 3-(2-(3,5-bis(trifluoromethyl)phenylamino)-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (yield: 59%).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with H2O (30 mL)
  3. washwashed with DCM (2×30 mL)
  4. filtrationthe resultant precipitate was filtered
  5. customdried

출처 및 근거

ORD 기록
ord-8e572dbd0ede49cbb7c60f542184e73a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133998B2

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