Chloroacetaldehyde → HCID 178457306, compound

HRID 1012979Notes

Reaction equation

HRID 1012979 reaction equation
Cl.[NH2:2][C:3]([C:6]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]([OH:24])[N:7]=1)([CH3:5])[CH3:4].CCN(CC)CC.[Cl:32][CH2:33][CH:34]=O.CC(O)=O.[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O>[Cl:32][CH2:33][CH2:34][NH:2][C:3]([C:6]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:13])[C:9]([OH:23])=[C:8]([OH:24])[N:7]=1)([CH3:4])[CH3:5]

Participants

7

Reactant 5

HCID 33ChloroacetaldehydeHCID 176Acetic AcidHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 178456881HCID 178456881, compound

Product 1

HCID 178457306HCID 178457306, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Procedure

To a methanolic solution of 2-(1-amino-1-methylethyl)-N-(4-fluorobenzyl)-5,6-dihydroxypyrimidine-4-carboxamide hydrochloride (prepared as described in WO2003035076 A1) Et3N (1 eq.), chloroacetaldehyde (2 eq.), AcOH (ca. 1.5 eq.) were added and subsequently NaBH3CN (1.5 eq.). The reaction mixture was stirred at room temperature overnight. To drive the reaction to completion a few drops of TFA were added and stirring was prolonged for a further 1.5 hours. MeOH was removed under reduced pressure to yield the title amine as crude. MS (ES) C17H20ClFN4O3 requires 383. Found: 384 (M+H+).

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas prolonged for a further 1.5 hours
  4. customMeOH was removed under reduced pressure

Sources & evidence

ORD record
ord-e02782bc722442ffa95542dd8ce04166
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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