Isopropylamine → HCID 136377082, compound

HRID 1409566Notes

Reaction equation

HRID 1409566 reaction equation
[CH3:1][CH:2]([NH2:4])[CH3:3].[C:5]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]1[NH:13][C:14](=[O:23])[C:15]([OH:22])=[C:16]([C:18](OC)=[O:19])[N:17]=1>>[CH:2]([NH:4][C:18]([C:16]1[N:17]=[C:12]([CH2:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:13][C:14](=[O:23])[C:15]=1[OH:22])=[O:19])([CH3:3])[CH3:1]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 136377081HCID 136377081, compound

Product 1

HCID 136377082HCID 136377082, compoundYield 22.3%

Conditions

Temperature
150 °C

Procedure

A sealed tube containing propan-2-amine (347 mg, 500 μl, 5.87 mmol), methyl 2-(biphenyl-2-ylmethyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (0.50 g, 148 μmol) was heated at 150° C. in a microwave oven for 10 minutes. The crude reaction mixture was cooled and evaporated to dryness. The solid residue 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 (0.012 g; 22%). LCMS: m/z=364 (MH+).

Workup

  1. customThe crude reaction mixture
  2. temperaturewas cooled
  3. customevaporated to dryness
  4. waitat room temperature for 1 h
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customtriturated with Et2O

Sources & evidence

ORD record
ord-02f26424804f4eb2a87de33b3032a41a
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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