Methylamine → HCID 136377080, compound

HRID 1409565Notes

Reaction equation

HRID 1409565 reaction equation
[CH3:1][NH2:2].[C:3]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]1[NH:11][C:12](=[O:21])[C:13]([OH:20])=[C:14]([C:16](OC)=[O:17])[N:15]=1>C1COCC1>[CH3:1][NH:2][C:16]([C:14]1[N:15]=[C:10]([CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[NH:11][C:12](=[O:21])[C:13]=1[OH:20])=[O:17]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 136377081HCID 136377081, compound

Product 1

HCID 136377080HCID 136377080, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

A sealed tube containing 2M solution of methylamine (2 ml, 4 mmol) in THF and methyl 2-(biphenyl-2-ylmethyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.05 g, 163 μmol, Eq: 1.00) was heated at 150° C. in a microwave oven for 15 min, cooled and filtered. The solid was stirred in MeOH, in the presence of Amberlyst 15 IE resin, at 60° C. for 5 min and then at room temperature for 1 h, filtered, evaporated to dryness and triturated with Et2O to give the title compound as a white solid (0.015 g; 27%). LCMS: m/z=336 (MH+).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. waitat room temperature for 1 h
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customtriturated with Et2O

Sources & evidence

ORD record
ord-050cc7bc529f465d86b07d1d018377d1
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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