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 3443

反応式

HRID 3443 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ede167eccc134bd3a388eacac4ece473
出典データセット
uspto-grants-1998_03
特許番号
US05733913

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