Water → 5-Methyl-2-phenylpyrimidine

HRID 1054107Notes

Reaction equation

HRID 1054107 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(O[CH:14]=[C:15]([CH3:18])[CH:16]=O)C.C[O-].[Na+].O>CO>[CH3:18][C:15]1[CH:14]=[N:9][C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:10][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80289Benzamidine, hydrochlorideHCID 5591983-Ethoxy-2-methyl-2-propenalHCID 10942334Sodium Methoxide

Product 1

HCID 8174325-Methyl-2-phenylpyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzamidine hydrochloride (500 mg, 3.19 mmol) and 3-ethoxy-2-methylacrylaldehyde (400 mg, 3.51 mmol) in Methanol (10 mL) was added a NaOMe-solution (30 percent in methanol) dropwise under stirring over 30 minutes. After stirring for 4 hours water (20 mL) was added and mixture was stirred for further 30 minutes at room temperature. After filtration the obtained precipitate was washed with water and dried. White solid. Yield: 220 mg, 41%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=2.34 (s, 3H), 7.44-7.54 (m, 3H), 8.37-8.45 (m, 2H), 8.64 (d, J=0.6 Hz, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=15.7, 128.1, 128.5, 128.8, 130.6, 137.9, 157.6, 162.7; (ESI): m/z=170.97 [M+H]+.

Workup

  1. additionwas added
  2. stirringmixture was stirred for further 30 minutes at room temperature
  3. filtrationAfter filtration the obtained precipitate
  4. washwas washed with water
  5. customdried

Sources & evidence

ORD record
ord-b6d8ee63f57f4ca5864e97cf3deebbd2
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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