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

HRID 617926

反応式

HRID 617926 の反応式
[NH2:1][C:2]1[C:3]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:28])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[N:7][C:6]=2[N:20]=1.[H-].[Na+].[C:31]([N:35]=[C:36]=[O:37])([CH3:34])([CH3:33])[CH3:32].C>CN(C=O)C.O>[C:31]([NH:35][C:36]([NH:1][C:2]1[C:3]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:28])=[CH:4][C:5]2[CH:10]=[N:9][C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[N:7][C:6]=2[N:20]=1)=[O:37])([CH3:34])([CH3:33])[CH3:32]

参加物

7

反応物 4

HCID 297MethaneHCID 24758Sodium hydrideHCID 62412tert-Butyl isocyanateHCID 53281146-(2,6-dichlorophenyl)-2-N-[3-(diethylamino)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine

生成物 1

HCID 53281153-Tert-butyl-1-[6-(2,6-dichlorophenyl)-2-{[3-(diethylamino)propyl]amino}pyrido[2,3-d]pyrimidin-7-yl]urea収率 27.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 7-amino-6-(2,6-dichlorophenyl)-2-(3-diethylamino-propylamino)-pyrido[2,3-d]pyrimidine (0.48 g) from Example 20 in DMF (5 mL) was added 60% sodium hydride suspension (46 mg), and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added t-butyl isocyanate (0.113 g), and the mixture was stirred for 18 hours. The reaction mixture was diluted with water and the insoluble material was collected by filtration. The solid was suspended in water (20 mL) and acidified with 1.ON HCl to form a solution. Activated charcoal was added to the solution, and the suspension filtered through celite, washing with water. The filtrate was made basic with 1.0 N NaOH, and the insoluble product was collected by filtration and washed with water. A 180-mg sample of the product was further purified by reverse phase preparative HPLC on a C18 reverse phase column, eluting with a solvent gradient starting from 86% of 0.1% trifluoroacetic acid in water/14% acetonitrile to 14% of 0.1% trifluoroacetic acid in water/86% acetonitrile over a 22-minute time period to afford 165 mg of 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-(3-diethylamino-propylamino)-pyrido[2,3-d]pyrimidin-7-yl]-urea, mp dec >80° C.

後処理

  1. stirringthe mixture was stirred for 18 hours
  2. filtrationthe insoluble material was collected by filtration
  3. customto form a solution
  4. filtrationthe suspension filtered through celite
  5. washwashing with water
  6. filtrationthe insoluble product was collected by filtration
  7. washwashed with water
  8. customA 180-mg sample of the product was further purified by reverse phase preparative HPLC on a C18 reverse phase column
  9. washeluting with a solvent gradient
  10. waitstarting from 86% of 0.1% trifluoroacetic acid in water/14% acetonitrile to 14% of 0.1% trifluoroacetic acid in water/86% acetonitrile over a 22-minute

出典と根拠

ORDレコード
ord-23bd3af9a53f45e580671bc2b92bd320
出典データセット
uspto-grants-1999_09
特許番号
US05952342

関連ノート

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