Sodium hydride → 3-Tert-butyl-1-[6-(2,6-dichlorophenyl)-2-{[3-(morpholin-4-yl)propyl]amino}pyrido[2,3-d]pyrimidin-7-yl]urea

HRID 617954

반응식

HRID 617954 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:28]([NH2:29])=[N:27][C:12]2[N:13]=[C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:15]=[CH:16][C:11]=2[CH:10]=1.[H-].[Na+].[C:32]([N:36]=[C:37]=[O:38])([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C>[C:32]([NH:36][C:37]([NH:29][C:28]1[C:9]([C:3]2[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:10][C:11]2[CH:16]=[N:15][C:14]([NH:17][CH2:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:13][C:12]=2[N:27]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 62412tert-Butyl isocyanateHCID 53281446-Arylpyrido[2,3-d]pyrimidine deriv. 42

생성물 1

HCID 53281453-Tert-butyl-1-[6-(2,6-dichlorophenyl)-2-{[3-(morpholin-4-yl)propyl]amino}pyrido[2,3-d]pyrimidin-7-yl]urea수율 79.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-(2,6-dichlorophenyl)-N2 -(3-morpholin-4-yl-propyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 58 in DMF (15 mL) was added one equivalent of 60% sodium hydride suspension (0.92 g). After stirring for approximately 1 hour at room temperature, one equivalent of tert-butyl isocyanate (0.230 g) was added, and the reaction was monitored by thin layer chromatography. After approximately 4 hours, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and water. The aqueous layer was washed several times with ethyl acetate. The ethyl acetate layers were combined, dried with magnesium sulfate, and concentrated in vacuo. Chromatography of the residue on silica gel using ethyl acetate followed by ethyl acetate:ethanol:triethylamine (18:2:1) gave 0.98 g of the title compound 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-(3-morpholin-4-yl-propylamino)-pyrido[2,3-d]pyrimidin-7-yl]-urea, CIMS (1% NH3 in CH4): 532=M+ +H, 531=M+, 433, 84 (Base); mp 236-240° C.

후처리

  1. waitAfter approximately 4 hours
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe aqueous layer was washed several times with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ad8cb8e75a3b4c95840dfe2a44908c58
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952342

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