Sodium ethoxide → tert-Butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930710노트

반응식

HRID 1930710 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[NH:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.O=[C:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]1[C:33](=O)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[O-]CC.[Na+]>C(O)C>[CH2:34]([C:33]1[C:21]2[CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25][C:20]=2[N:17]=[C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:18]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

참가 물질

5

반응물 3

HCID 2723922Sodium ethoxideHCID 59333761Tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylateHCID 178493227HCID 178493227, 화합물

생성물 1

HCID 59333725tert-Butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate수율 92%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (300 mg, 1.22 mmol, example 43a), tert-butyl 4-oxo-3-(2-phenylacetyl)piperidine-1-carboxylate (466 mg, 1.47 mmol, example 41d) and sodium ethoxide (83 mg, 1.22 mmol) in ethanol (4 mL) were heated at 100° C. in a microwave reactor for 20 minutes. The reaction mixture was allowed to reach room temperature and the solvent was evaporated under reduced pressure. The crude was dissolved in ethyl acetate and washed with water. The organic phase was dried under MgSO4 and the solvent was evaporated under reduced pressure yielding tert-butyl 4-benzyl-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (590 mg, 92%) which was used in the subsequent step as such. MS (ES+) m/z 527.3 (M+H)+

후처리

  1. customto reach room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe crude was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe organic phase was dried under MgSO4
  6. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-0a5a5da9c18b466ba64f8af44c1415ad
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188101B2

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