2-Chloro-4-aminopyrimidine → 2-O-Methylcytosine

HRID 1396939Notes

Reaction equation

HRID 1396939 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][O-:10].[Na+]>CO>[CH3:9][O:10][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 3457522-Chloro-4-aminopyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 1606792-O-MethylcytosineYield 50.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-pyrimidinamine (150 mg, 1.158 mmol) and sodium methoxide (188 mg, 3.47 mmol) in methanol (2.9 ml) was heated to 100° C. via a microwave reactor for 40 min. The crude product mixture was purified by RP-HPLC to give 2-(methyloxy)-4-pyrimidinamine (73 mg, 0.583 mmol, 50% yield). MS (ES+) m/z 126.0 (MH+).

Workup

  1. customThe crude product mixture was purified by RP-HPLC

Sources & evidence

ORD record
ord-c3f8d5c3efa042679a4b7def8999b91a
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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