Phenolate Sodium → 6-Methyl-4-phenoxy-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine

HRID 1977690Notes

Reaction equation

HRID 1977690 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)[N:3]=1.[O-:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Na+]>O>[CH3:8][C:6]1[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)[N:3]=[C:2]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4445035Phenolate SodiumHCID 219951684-Chloro-6-methyl-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine

Product 1

HCID 219952196-Methyl-4-phenoxy-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amineYield 12.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Chloro-6-methyl-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine (0.30 g, 0.97 mmol) was added to a solution of sodium phenoxide (0.97 mmol) [prepared from phenol (0.091 g, 0.97 mmol) and NaH (60% in mineral oil; 0.039 g, 0.97 mmol)], and heated to 80° for 17 h with stirring. Water was added and the mixture was extracted with CH2CH2 (2×30 ml), the organic phases were dried (MgSO4) and evaporated to a yellow oil. The residue was subjected to chromatography (silica, 2% methanol/CH2CH2) to give the title compound (0.046 g). A portion was recrystallised from methanol to give an off white crystalline solid m.p. 175°. δH (CDCl3) 2.38 (3H, s), 3.64 (6H, s), 3.77 (3H, s), 6.19 (1H, s), 6.78 (2H, s), 6.95 (1H, s), 7.15 (2H, d, J 7.5 Hz), 7.23 (1H, m) and 7.39 (2H, t, J 7.5 Hz).

Workup

  1. temperatureheated to 80° for 17 h
  2. extractionthe mixture was extracted with CH2CH2 (2×30 ml)
  3. dry with materialthe organic phases were dried (MgSO4)
  4. customevaporated to a yellow oil

Sources & evidence

ORD record
ord-f003db50922342c3a725b20ded90f0b2
Source dataset
uspto-grants-2001_05
Patent number
US06235746B1

Reaction notes

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