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

HRID 1666205Notes

Reaction equation

HRID 1666205 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%.

Workup

  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)

Sources & evidence

ORD record
ord-3748827f543049938de508b09c604030
Source dataset
uspto-grants-2011_10
Patent number
US08044056B2

Reaction notes

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