Phenyl isocyanate → 3-[6-(2,6-Dichlorophenyl)-2-{[4-(diethylamino)butyl]amino}pyrido[2,3-d]pyrimidin-7-yl]-1-phenylurea

HRID 617950

反応式

HRID 617950 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][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[N:15]=[CH:16][C:11]=2[CH:10]=1.[H-].[Na+].[C:32]1([N:38]=[C:39]=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:28]([NH:29][C:39]([NH:38][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:40])=[N:27][C:12]2[N:13]=[C:14]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[N:15]=[CH:16][C:11]=2[CH:10]=1

参加物

5

反応物 3

HCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 53281336-(2,6-dichlorophenyl)-2-N-[4-(diethylamino)butyl]pyrido[2,3-d]pyrimidine-2,7-diamine

生成物 1

HCID 53281373-[6-(2,6-Dichlorophenyl)-2-{[4-(diethylamino)butyl]amino}pyrido[2,3-d]pyrimidin-7-yl]-1-phenylurea収率 66.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-(2,6-dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine (1.0 g) from Example 53 in DMF (15 mL) was added one equivalent of 60% sodium hydride suspension (0.93 g). After stirring for approximately 1 hour at room temperature, one equivalent of phenyl isocyanate (0.275 g) was added, and the reaction was monitored by thin layer chromatography. After approximately 24 hours, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, and this solution was washed several times, first with water and then a saturated solution of sodium chloride. The ethyl acetate layer was dried with magnesium sulfate and concentrated in vacuo. Chromatography of the residue over silica gel using ethyl acetate:methanol:triethylamine (90:10:1) followed by ethyl acetate:ethanol:triethylamine (9:2:1) gave 0.8461 g of the title compound 1-[6-(2,6-dichlorophenyl)-2-(4-diethylamino-butylamino)-pyrido[2,3-d]pyrimidin-7-yl]-3-phenyl-urea, ESMS (20/80 MeOH/CH3CN+0.1% AcOH) M+ +H=552 (Base), 433; mp 81-87.5° C.

後処理

  1. waitAfter approximately 24 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthis solution was washed several times
  5. dry with materialThe ethyl acetate layer was dried with magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5548da6b16b449899ade1b28af2b95a4
出典データセット
uspto-grants-1999_09
特許番号
US05952342

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