Benzaldehyde → 6-Amino-9-(3-{benzyl[2-(dimethylamino)ethyl]amino}propyl)-2-butoxy-7,9-dihydro-8h-purin-8-one

HRID 562494Notes

Reaction equation

HRID 562494 reaction equation
Cl.[NH2:2][C:3]1[N:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:9]=[C:8]2[C:4]=1[NH:5][C:6](=[O:26])[N:7]2[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24].[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.CO>[NH2:2][C:3]1[N:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:9]=[C:8]2[C:4]=1[NH:5][C:6](=[O:26])[N:7]2[CH2:17][CH2:18][CH2:19][N:20]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:21][CH2:22][N:23]([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 1317292896-Amino-2-butoxy-9-(3-{[2-(dimethylamino)ethyl]amino}propyl)-7,9-dihydro-8H-purin-8-one, hydrochloride

Product 1

HCID 249646906-Amino-9-(3-{benzyl[2-(dimethylamino)ethyl]amino}propyl)-2-butoxy-7,9-dihydro-8h-purin-8-oneYield 59.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product from step (iii) (0.1 g) and benzaldehyde (0.0362 g, 0.0347 ml) were combined in NMP (4 mL) and stirred at RT for 15 mins. Sodium triacetoxyborohydride (0.0904 g) was added. The reaction mixture was stirred for 16 h. The reaction mixture was diluted with methanol and purified by RP-prep-HPLC 75:05 NH3:acetonitrile over 15 mins to give title compound (0.068 g)

Workup

  1. stirringThe reaction mixture was stirred for 16 h
  2. custompurified by RP-prep-HPLC 75:05 NH3

Sources & evidence

ORD record
ord-3a70e952d2aa4bc686d2f57b9cc4286f
Source dataset
uspto-grants-2011_11
Patent number
US08067411B2

Reaction notes

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