Methylamine → HCID 86710264, compound

HRID 1409563Notes

Reaction equation

HRID 1409563 reaction equation
[CH3:1][NH2:2].[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]1[N:11]([CH3:22])[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:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:11]([CH3:22])[C:12](=[O:21])[C:13]=1[OH:20])=[O:17]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86710263HCID 86710263, compound

Product 1

HCID 86710264HCID 86710264, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A sealed tube containing 2M solution of methylamine (1.71 ml, 3.42 mmol) in THF and methyl 2-(biphenyl-2-ylmethyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.1 g, 285 μmol) was heated at 100° C. in a microwave oven for 20 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 (0.040 g; 40%). LCMS: m/z=351 (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-5e8336c88aef46a58f5233187a22536f
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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