Methylamine → HCID 136268167, compound

HRID 1409580Notes

Reaction equation

HRID 1409580 reaction equation
[CH:1]1([CH2:7][C:8]2[NH:9][C:10](=[O:19])[C:11]([OH:18])=[C:12]([C:14]([O:16]C)=O)[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:20][NH2:21]>CO>[CH3:20][NH:21][C:14]([C:12]1[N:13]=[C:8]([CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[NH:9][C:10](=[O:19])[C:11]=1[OH:18])=[O:16]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 136377091HCID 136377091, compound

Product 1

HCID 136268167HCID 136268167, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of methyl 2-(cyclohexylmethyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (30 mg, 113 μmol), methylamine (2M in THF) (1.5 ml, 3.00 mmol) and MeOH (10 ml) was heated in a microwave oven at 140° C. for 40 min. The cooled reaction mixture was concentrated in vacuo. The residue was heated in a mixture of MeOH and Amberlyst until all the product had dissolved. The resin was removed by filtration and the filtrate was evaporated to dryness under reduced pressure to give the title compound as an off-white solid (0.011 g; 35% with 95% purity). LCMS: m/z=266 (MH+).

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated in vacuo
  3. temperatureThe residue was heated in a mixture of MeOH and Amberlyst until all the product
  4. dissolutionhad dissolved
  5. customThe resin was removed by filtration
  6. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e24726f7a05744bdaa37c4e602e7bc41
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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