Water → [1-(4-Chloro-phenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester

HRID 1749103ノート

反応式

HRID 1749103 の反応式
[C:1]([O:5][C:6](=[O:37])[N:7]([C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:24](=[O:29])[NH:25][CH2:26][C:27]=2[N:28]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:41].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:37])[N:7]([C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:24](=[O:29])[N:25]([CH3:41])[CH2:26][C:27]=2[N:28]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[O:17][CH3:18])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70981608[1-(4-Chloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester

生成物 1

HCID 70980679[1-(4-Chloro-phenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester収率 39.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of [1-(4-chloro-phenyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (Example 21, low RF compound from Step 1) (120 mg, 0.23 mmol) in DMF (3 mL) was added NaH (60% dispersion in oil, 14 mg, 0.34 mmol, 1.5 equiv) and the reaction mixture was stirred for 1 h. Iodomethane (30 μL, 0.46 mmol, 2 equiv) was added and stirring was continued overnight. Water was added and the product was extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and the solvent evaporated. The crude material was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-100%) to afford [1-(4-chloro-phenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (49 mg). MS: [M+H]+=539.

後処理

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionthe product was extracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude material was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-100%)

出典と根拠

ORDレコード
ord-42bb57cdecdf413686aca8db08d7fb05
出典データセット
uspto-grants-2015_10
特許番号
US09155743B2

反応ノート

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