Triethylamine → HCID 69015576, compound

HRID 1374867Notes

Reaction equation

HRID 1374867 reaction equation
[NH2:1][C@@H:2]([C:6]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=[O:19])[C:9]([CH3:20])=[C:8]([CH3:21])[N:7]=1)[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.[CH3:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1>C(Cl)Cl>[CH2:12]([N:11]1[C:10](=[O:19])[C:9]([CH3:20])=[C:8]([CH3:21])[N:7]=[C:6]1[C@H:2]([NH:1][C:34](=[O:35])[C:33]1[CH:37]=[CH:38][C:30]([CH3:29])=[CH:31][CH:32]=1)[CH:3]([CH3:4])[CH3:5])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 69018345HCID 69018345, compound

Product 1

HCID 69015576HCID 69015576, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-((R)-1-amino-2-methyl-propyl)-3-benzyl-5,6-dimethyl-3H-pyrimidin-4-one (50 mg, 0.175 mMol) and triethylamine (49 μL, 0.350 mMol) in CH2Cl2 was add 4-methyl-benzoyl chloride (21 μL, 0.157 mMol) was added. The reaction was stirred at RT for 48 h, quenched with water and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried (Na2SO4), filtered, and evaprated to give the title compound (50 mg, 72%) as colorless oil. MS (ES) m/e 404.2 (M+H)+.

Workup

  1. additionwas added
  2. customquenched with water
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d13b6f4744604fdeb9a1451714aa5ea2
Source dataset
uspto-grants-2007_01
Patent number
US07166595B2

Reaction notes

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