Methanol → 2-(4-amino-2,5-dimethylphenoxy)-5-chloro-N-ethyl-N-methylpyrimidin-4-amine

HRID 12088Notes

Reaction equation

HRID 12088 reaction equation
[Cl:1][C:2]1[C:3]([N:20]([CH2:22][CH3:23])[CH3:21])=[N:4][C:5]([O:8][C:9]2[CH:14]=[C:13]([CH3:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=2[CH3:19])=[N:6][CH:7]=1.CO>Cl>[NH2:16][C:12]1[C:13]([CH3:15])=[CH:14][C:9]([O:8][C:5]2[N:4]=[C:3]([N:20]([CH2:22][CH3:23])[CH3:21])[C:2]([Cl:1])=[CH:7][N:6]=2)=[C:10]([CH3:19])[CH:11]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 67026756HCID 67026756, compound

Product 1

HCID 670266552-(4-amino-2,5-dimethylphenoxy)-5-chloro-N-ethyl-N-methylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 8.86 g (20 mmol) 5-chloro-2-(2,5-dimethyl-4-nitrophenoxy)-N-ethyl-N-methylpyrimidin-4-amine in 50 ml hydrochloric acid and 50 ml methanol 13.5 g (60 mmol) tin-(II)-dichloro dihydrate was added and the mixture was refluxed for 4 h. After cooling down to ambient temperature the formed precipitate was filtered by suction, solved in water and brought to pH 8 with aqueous solution of sodium hydroxide. Ethyl acetate was added and the organic layer was separated, dried over magnesium sulfate, concentrated in vacuo and column chromatography (cyclohexane/ethyl acetate, 1:1) yielded 4.6 g (72%) with a purity of 96% log P (pH=2.3)=1.88.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. filtrationwas filtered by suction
  3. additionEthyl acetate was added
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo and column chromatography (cyclohexane/ethyl acetate, 1:1)
  7. customyielded 4.6 g (72%) with a purity of 96% log P (pH=2.3)=1.88

Sources & evidence

ORD record
ord-7e6296a5515441d5b10b47b9b173f03f
Source dataset
uspto-grants-2010_06
Patent number
US07727986B2

Reaction notes

Loading…