Dimethylamine → 9-{2-[1-(4-Dimethylaminomethylbenzyl)piperidin-4-yl]ethyl}-8-methoxy-2-(2-methoxyethoxy)-9H-purin-6-ylamine

HRID 1666205ノート

反応式

HRID 1666205 の反応式
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:33][CH3:34])[N:6]2[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[CH2:20][CH2:19]1.[CH3:35][NH:36][CH3:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[CH3:35][N:36]([CH2:29][C:28]1[CH:31]=[CH:32][C:25]([CH2:24][N:21]2[CH2:20][CH2:19][CH:18]([CH2:17][CH2:16][N:6]3[C:5]([O:33][CH3:34])=[N:4][C:3]4[C:7]3=[N:8][C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:10][C:2]=4[NH2:1])[CH2:23][CH2:22]2)=[CH:26][CH:27]=1)[CH3:37]

参加物

6

反応物 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 592880284-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)benzaldehyde

生成物 1

HCID 592880309-{2-[1-(4-Dimethylaminomethylbenzyl)piperidin-4-yl]ethyl}-8-methoxy-2-(2-methoxyethoxy)-9H-purin-6-ylamine収率 87%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The compound (0.31 g, 1.66 mmol) obtained in Step (ii) was dissolved in THF (10 ml), and thereto were added at 0° C. dimethylamine (2M THF solution, 2.62 ml, 5.24 mmol) and sodium triacetoxy borohydride (0.56 g, 2.62 mmol), and the mixture was stirred at room temperature for 20 hours. The mixture was cooled to 0° C., and thereto was added a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted three times with chloroform/ethanol=3/1. The extract was dried over magnesium sulfate, concentrated, and purified by silica gel column (chloroform/methanol/28% aqueous ammonia=100/5/0 to 100/5/1) to give the title compound (0.28 g, 0.57 mmol) as a white solid. Yield: 87%.

後処理

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionthe mixture was extracted three times with chloroform/ethanol=3/1
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column (chloroform/methanol/28% aqueous ammonia=100/5/0 to 100/5/1)

出典と根拠

ORDレコード
ord-3748827f543049938de508b09c604030
出典データセット
uspto-grants-2011_10
特許番号
US08044056B2

反応ノート

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