Phosphorus oxychloride → 4-Chloro-6-methyl-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine

HRID 619375Notes

Reaction equation

HRID 619375 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[NH:5][C:4](=O)[CH:3]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[N:5]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1360672746-Methyl-2-(3,4,5-trimethoxyphenylamino)-4(3H)pyrimidinone

Product 1

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

Procedure

6-Methyl-2-(3,4,5-trimethoxyphenylamino)-4(3H)pyrimidinone (1.0 g, 3.63 mmol) was dissolved in phosphoryl chloride and heated to 100° for 2 h. The mixture was cooled to room temperature and evaporated in vacuo to a viscous oil. The oil was dissolved in CH2CH2 (50 ml) and washed twice with saturated aqueous NaHCO3, the organic phases dried (MgSO4) and concentrated in vacuo. The residue was subjected to column chromatography (silica, 2% methanol/CH2CH2) to afford the title compound as an off white solid (1.03 g). A small amount was recrystallised from ethyl acetate to give fine off-white needles. m.p. 195-196°. δH (CDCl3) 2.40 (3H, s), 3.82 (3H, s), 3.88 (6H, s), 6.64 (1H, s), 6.95 (2H, s), and 7.07 (1H, br s).

Workup

  1. temperatureheated to 100° for 2 h
  2. customevaporated in vacuo to a viscous oil
  3. dissolutionThe oil was dissolved in CH2CH2 (50 ml)
  4. washwashed twice with saturated aqueous NaHCO3
  5. dry with materialthe organic phases dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f532eb28b5c442a396a27b47703f6d4a
Source dataset
uspto-grants-1999_09
Patent number
US05958935

Reaction notes

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