Water → HCID 17979299, compound

HRID 16431Notes

Reaction equation

HRID 16431 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([Cl:12])[N:3]=1.[BH4-].[Na+].C(OCC)(=O)C.O>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:12])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 239687Methyl 2-amino-6-chloropyrimidine-4-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 17979299HCID 17979299, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.5 g (55.97 mmol) of methyl 2-amino-6-chloropyrimidine-4-carboxylate (prepared according to G. Doyle Daves, Fred Baiocchi, Roland K. Robins, and C. C. Cheng, J. Org. Chem., 26 (1961), 2755-2763) are initially charged in 450 ml of ethanol. 21.17 g (559.74 mmol) of sodium borohydride are added, and the mixture is stirred at room temperature for 2 hours. 500 ml of ethyl acetate and 500 ml of water are added, and the solution is stirred for 30 minutes. The phases are separated and the aqueous phase is extracted three times with ethyl acetate (in each case 100 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated. This gives 7.21 g (85% of theory) of product.

Workup

  1. stirringthe solution is stirred for 30 minutes
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted three times with ethyl acetate (in each case 100 ml)
  4. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fb2e5cdb8bf1472e836aa1162ff21f83
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Reaction notes

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