Methyl iodide → 2,3-Dimethyl-6-phenyl-5-(prop-2-yn-1-yl)pyrimidin-4(3H)-one

HRID 1608875

Reaction equation

HRID 1608875 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([CH2:9][C:10]#[CH:11])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[C:18](=O)([O-])[O-].[K+].[K+].CI.C(C(C)=O)C>O>[CH3:1][C:2]1[N:7]([CH3:18])[C:6](=[O:8])[C:5]([CH2:9][C:10]#[CH:11])=[C:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 1356894052-methyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone

Product 1

HCID 200851942,3-Dimethyl-6-phenyl-5-(prop-2-yn-1-yl)pyrimidin-4(3H)-oneYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.76 g (3.4 mmol) of 2-methyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone, 0.72 g (5.2 mmol) of anhydrous potassium carbonate, 0.32 mL (5.1 mmol) of methyl iodide and 20 mL of methyl ethyl ketone was heated at reflux for 6 h. The mixture was cooled, diluted with 40 mL of water and extracted with two 60 mL portions of ethyl acetate. The ethyl acetate extracts were dried and rotovaped to leave 0.75 g of crude product. This material was purified by flash chromatography on silica gel to afford 0.71 g of 2,3-dimethyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone as a white solid, mp 142°-144° C., 1H-NMR (CDCl3) δ2.10(3H,t,J=4), 2.60(3H, s), 3.40(2H,d,J=4), 3.60(3H,s), 7.45(3H,m), 7.65(2H, m); IR(nujol) 3200, 1650 cm-1. Calculated for C15H14N2O: C 75.61, H 5.92, N 11.76. Found: C 75.33, H 5.72, N 11.63.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 h
  3. temperatureThe mixture was cooled
  4. extractionextracted with two 60 mL portions of ethyl acetate
  5. dry with materialThe ethyl acetate extracts were dried
  6. customto leave 0.75 g of crude product
  7. customThis material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f86a0cd8ee3b479eaa06f7abed52eb1c
Source dataset
uspto-grants-1995_03
Patent number
US05397767

Linked notes

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