2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 6-[(2,4-Dichloro-5-thiazolyl)hydroxymethyl]-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, ethyl ester

HRID 131626

반응식

HRID 131626 반응식
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][S:11][C:5]=2[N:4]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:3]1=[O:21].[Cl:22][C:23]1[S:24][C:25]([CH:29]=[O:30])=[C:26]([Cl:28])[N:27]=1.CN1C(=O)N(C)CCC1.[Li+].CC([N-]C(C)C)C>C1COCC1.C(O)(=O)C>[Cl:22][C:23]1[S:24][C:25]([CH:29]([OH:30])[C:10]2[S:11][C:5]3[N:4]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:3](=[O:21])[N:2]([CH3:1])[C:7](=[O:8])[C:6]=3[C:9]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:26]([Cl:28])[N:27]=1

참가 물질

7

반응물 4

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehydeHCID 2724682Lithium diisopropylamideHCID 5282568Ethyl 3-methyl-1-(2-methylpropyl)-2,4-dioxo-1,2,3,4-tetrahydro-thieno[2,3-d]pyrimidine-5-carboxylate

생성물 1

HCID 866035756-[(2,4-Dichloro-5-thiazolyl)hydroxymethyl]-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid, ethyl ester수율 18.9%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 3-methyl-1-(2-methylpropyl)-2,4-dioxo-1,2,3,4-tetrahydro-thieno[2,3-d]pyrimidine-5-carboxylate (1.5 g), 2,4-dichlorothiazole-5-carboxaldehyde (1.75 g) and DMPU (1.2 ml) in THF (25 ml) at −78° C., was added LDA (10 mmol). Acetic acid (3 ml) was added and the mixture allowed to warm to ambient temperature. The mixture was then partitioned between ethyl acetate and water, the organics were collected, dried over magnesium sulphate and concentrated to dryness. The residue was purified by normal phase chromatography (3:1 i-hexane:ethyl acetate) to give the sub-title compound as a yellow foam (0.45 g).

후처리

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. customthe organics were collected
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by normal phase chromatography (3:1 i-hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-03a4f0a480934016888a6fbafb905ed1
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384951B2

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