Methyl iodide → [(4S,5R)-1,4,5-trimethyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

HRID 1255793ノート

反応式

HRID 1255793 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[N:9]([CH3:25])[C:10](=[O:24])[CH2:11][C@@:12]([CH3:23])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[N:13]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].[CH3:28]C([N-]C(C)C)C.IC>C1COCC1>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[N:9]([CH3:25])[C:10](=[O:24])[C@H:11]([CH3:28])[C@@:12]([CH3:23])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[N:13]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 57496576[(S)-1,4-dimethyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester2 回

生成物 1

HCID 57496601[(4S,5R)-1,4,5-trimethyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of [(S)-1,4-dimethyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (110 mg, intermediate E1) in THF (3.0 ml) was added at −78° C. a solution of LDA (3 eq., 1.95 ml) and stirring was continued for 1 h. The mixture was treated at −78° C. with a solution of iodomethane (38 μl) in THF (2.0 ml) and stirring was continued at the same temperature for 1.5 h. The mixture was quenched with saturated aqueous NH4Cl, extracted with diethyl ether, the organic layer was dried and evaporated. The residue was chromatographed on silica using n-heptane/ethyl acetate (5:1) to give [(4S,5R)-1,4,5-trimethyl-4-(3-nitro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyrimidin-2-yl]-carbamic acid tert-butyl ester (72 mg) as a colorless foam. MS (ESI): m/z=377.4 [ M+H]+. The hydrogenation of the nitro group to give the aniline (intermediate F) was carried out as described in Scheme 1.

後処理

  1. stirringstirring
  2. waitwas continued at the same temperature for 1.5 h
  3. customThe mixture was quenched with saturated aqueous NH4Cl
  4. extractionextracted with diethyl ether
  5. customthe organic layer was dried
  6. customevaporated
  7. customThe residue was chromatographed on silica

出典と根拠

ORDレコード
ord-de1c4c951eac40b5b15d5d9f2788d426
出典データセット
uspto-grants-2013_06
特許番号
US08461160B2

反応ノート

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