Benzaldehyde → 6-Amino-9-{3-[benzyl(3-morpholin-4-ylpropyl)amino]propyl}-2-butoxy-7,9-dihydro-8H-purin-8-one

HRID 562490Notes

Reaction equation

HRID 562490 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:29])[N:6]2[CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.CO>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:29])[N:6]2[CH2:16][CH2:17][CH2:18][N:19]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:20][CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 669622806-Amino-2-butoxy-9-[3-(3-morpholin-4-yl-propylamino)-propyl]-7,9-dihydro-purin-8-one

Product 1

HCID 249636146-Amino-9-{3-[benzyl(3-morpholin-4-ylpropyl)amino]propyl}-2-butoxy-7,9-dihydro-8H-purin-8-oneYield 55.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-Amino-2-butoxy-9-[3-(3-morpholin-4-yl-propylamino)-propyl]-7,9-dihydro-purin-8-one (0.1 g), Benzaldehyde (0.03125 g, 0.03005 ml) were combined in NMP (1.5 mL) and stirred at RT for 15 mins. Sodium triacetoxyborohydride (0.078 g) was added and the reaction mixture was stirred for 16 h. The reaction mixture was diluted with methanol and purified by RPHPLC to give the title compound (0.068 g)

Workup

  1. stirringthe reaction mixture was stirred for 16 h
  2. custompurified by RPHPLC

Sources & evidence

ORD record
ord-b73d67006ed54e9ca7b02d5f3774cfba
Source dataset
uspto-grants-2011_11
Patent number
US08067411B2

Reaction notes

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