Sodium cyanoborohydride → HCID 178457325, compound

HRID 1012984Notes

Reaction equation

HRID 1012984 reaction equation
[NH2:1][C:2]([C:5]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2S(C)(=O)=O)=[O:12])[C:8]([OH:26])=[C:7]([OH:27])[N:6]=1)([CH3:4])[CH3:3].[CH2:28]([O:35][CH2:36][CH2:37][CH:38]=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([BH3-])#N.[Na+]>>[CH2:28]([O:35][CH2:36][CH2:37][CH2:38][NH:1][C:2]([C:5]1[N:10]=[C:9]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[O:12])[C:8]([OH:26])=[C:7]([OH:27])[N:6]=1)([CH3:4])[CH3:3])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 108882613-(Benzyloxy)propanalHCID 178456882HCID 178456882, compound

Product 1

HCID 178457325HCID 178457325, compound

Procedure

A methanolic solution of 2-(1-amino-1-methylethyl)-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide (prepared as described in WO2003035076 A1) was treated with 3-(benzyloxy)propanal (1.5 eq.) and sodium cyanoborohydride (1.5 eq.). The mixture was stirred at room temperature overnight, solution was applied on a cation exchange resin. The resin was washed with methanol and desired product was eluted with 2 N ammonia solution in methanol. Evaporation of appropriate fractions followed by trituration with Et2O gave intermediate 2-(1-{[3-(benzyloxy)propyl]amino}-1-methylethyl)-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide. MS (ES) C25H29FN4O4 requires 468. Found: 469 (M+H+). The crude organic product was taken in methanol, treated with 1 eq. of 6N HCl and stirred under hydrogen atmosphere in the presence of catalytic amount of 10% palladium on charcoal. After overnight stirring, mixture was filtered through celite, filtrate was concentrated under reduced pressure and purified by cation exchange resin. The resin was washed with methanol and desired product was eluted with 2 N ammonia solution in methanol. Evaporation of appropriate fractions followed by trituration with Et2O gave title compound as a pink solid. MS (ES) C18H23FN4O4 requires 378. Found: 379 (M+H+).

Workup

  1. washThe resin was washed with methanol and desired product
  2. washwas eluted with 2 N ammonia solution in methanol
  3. customEvaporation of appropriate fractions

Sources & evidence

ORD record
ord-2b3997207eb64cfa8d438eceb7394dc9
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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