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

HRID 3439

반응식

HRID 3439 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][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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e67c6fe74c75494e9570b2bde6a06c78
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733913

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