Acetonitrile → Methyl 2-amino-5-(benzyloxy)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate

HRID 1409589Notes

Reaction equation

HRID 1409589 reaction equation
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12](S(C)(=O)=O)=[N:11][C:10]=1[C:21]([O:23][CH3:24])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC#[N:27]>>[CH3:24][O:23][C:21]([C:10]1[N:11]=[C:12]([NH2:27])[N:13]([CH3:16])[C:14](=[O:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 86710287Methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Product 1

HCID 86710288Methyl 2-amino-5-(benzyloxy)-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate

Procedure

In a round-bottomed flask, methyl 5-(benzyloxy)-1-methyl-2-(methylsulfonyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate (3.65 g, 10.4 mmol) was combined with CH3CN (50 ml) to give a colorless solution. Gaseous ammonia was bubbled at 25° C. for 20 min. The crude material was purified by flash chromatography (silica gel, 30% to 50% EtOAc in hexanes) and then through a second column (5% MeOH/DCM) to give the title product as a white solid. LCMS: m/z=290 (MH+).

Workup

  1. customto give a colorless solution
  2. customGaseous ammonia was bubbled at 25° C. for 20 min
  3. customThe crude material was purified by flash chromatography (silica gel, 30% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cbd73771b52f46128271b1096a89920f
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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