2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → 1,2,3,4-Tetrahydro-6-[hydroxy(1-phenyl-1H-pyrazol-4-yl)methyl]-3-methyl-1-(1-methylethyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid ethyl ester

HRID 131628

반응식

HRID 131628 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:13](=[O:15])[N:12]([CH3:16])[C:11](=[O:17])[N:10]([CH:18]([CH3:20])[CH3:19])[C:9]=2[S:8][CH:7]=1)=[O:5])[CH3:2].[C:21]1([N:27]2[CH:31]=[C:30]([CH:32]=[O:33])[CH:29]=[N:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN1CCCN(C)C1=O.[Li+].CC([N-]C(C)C)C>C1COCC1.O.C(O)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:13](=[O:15])[N:12]([CH3:16])[C:11](=[O:17])[N:10]([CH:18]([CH3:19])[CH3:20])[C:9]=2[S:8][C:7]=1[CH:32]([OH:33])[C:30]1[CH:29]=[N:28][N:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:31]=1)=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 9520891-Phenyl-1H-pyrazole-4-carbaldehydeHCID 2724682Lithium diisopropylamideHCID 16102858Ethyl 1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

생성물 1

HCID 693098291,2,3,4-Tetrahydro-6-[hydroxy(1-phenyl-1H-pyrazol-4-yl)methyl]-3-methyl-1-(1-methylethyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylic acid ethyl ester수율 73.4%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1,2,3,4-tetrahydro-3-methyl-1-(1-methylethyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid ethyl ester (2.0 g), 1-phenyl-1H-pyrazole-4-carboxaldehyde (1.39 g) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.63 ml) in anhydrous THF (35 ml) was added a 2.0M solution of LDA (3.72 ml) at −78° C. under nitrogen and the resulting mixture stirred for 3 hr. Glacial acetic acid (1.5 ml) was added, the mixture allowed to warm to room temperature, diluted with water and extracted with ethyl acetate, the organic extracts washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with i-hexane/ethyl acetate (4:1) followed by i-hexane/ethyl acetate (1:1) to give the sub-title compound (2.32 g).

후처리

  1. extractionextracted with ethyl acetate
  2. washthe organic extracts washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica
  7. washeluting with i-hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-55a9774b0d4241e794af27f34858bb57
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384951B2

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