Lithium borohydride → (6-Aminopyrimidin-4-yl)methanol

HRID 2366241Notes

Reaction equation

HRID 2366241 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](OC)=[O:9])[CH:3]=1.[Li+].[BH4-]>CO>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 21955432Methyl 6-aminopyrimidine-4-carboxylate

Product 1

HCID 21934615(6-Aminopyrimidin-4-yl)methanolYield 61.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of methyl 6-aminopyrimidine-4-carboxylate (2.0 g, 13 mmol) in MeOH (20 mL) at 25° C., was added LiBH4 (0.85 g, 39 mmol). After addition, the resulting mixture was allowed to stir at 70° C. for 16 hours. TLC indicated the starting material was consumed completely at this point. Solvents were removed under reduced pressure and the residue was purified via chromatography column on silica gel eluting with a 5% gradient of methanol in dichloromethane to give the desired alcohol as pale yellow oil (1.0 g, 61% yield). LCMS (ESI) m/z: 126.1 [M+H+].

Workup

  1. additionAfter addition
  2. customwas consumed completely at this point
  3. customSolvents were removed under reduced pressure
  4. customthe residue was purified via chromatography column on silica gel eluting with a 5% gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-4844b7b696b44e889a7cf08ae9bb0d30
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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