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

反応式

HRID 131628 の反応式
[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]

参加物

8

反応物 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

生成物 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 ester収率 73.4%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-55a9774b0d4241e794af27f34858bb57
出典データセット
uspto-grants-2008_06
特許番号
US07384951B2

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