HCID 385229, compound → HCID 385226, compound

HRID 1421879Notes

Reaction equation

HRID 1421879 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([CH2:15][OH:16])[CH2:13][C:12](=[O:14])[CH2:11]2)[CH:5]=[C:4]([Cl:17])[N:3]=1.[BH4-].[Na+].Cl.C(O)C>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2([CH2:15][OH:16])[CH2:11][CH:12]([OH:14])[CH2:13]2)[CH:5]=[C:4]([Cl:17])[N:3]=1

Participants

5

Reactant 3

HCID 385229HCID 385229, compoundHCID 4311764Sodium borohydrideHCID 21887872Ethanol hydrochloride

Product 1

HCID 385226HCID 385226, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-6-chloro-4-[[(1-hydroxymethyl-3-oxo-1-cyclobutyl)methyl]-amino]pyrimidine (2.21 g, 8.26 mmol) was dissolved in ethanol (80 ml) and sodium borohydride (0.31 g, 8.26 mmol) was added portionwise under ice-cooling. The mixture was stirred at room temperature for 30 minutes. The mixture was neutralized with hydrochloric acid-ethanol. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:7) to give white crystals (2.14 g, quantitative), m.p. 136-139° C. (ethyl acetate).

Workup

  1. temperaturecooling
  2. distillationThe solvent was distilled away under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:7)
  4. customto give white crystals (2.14 g, quantitative), m.p. 136-139° C. (ethyl acetate)

Sources & evidence

ORD record
ord-9368c8825f2046279f7fbb546fde140b
Source dataset
uspto-grants-2000_06
Patent number
US06080750

Reaction notes

Loading…