Phosphorus oxychloride → 4-Chloro-5,6-dimethyl-N-(4-methyl-2-thiazolyl)-2-pyrimidinamine

HRID 275926Notes

Reaction equation

HRID 275926 reaction equation
[CH3:1][C:2]1[C:3](O)=[N:4][C:5]([NH:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[N:6][C:7]=1[CH3:8].P(Cl)(Cl)([Cl:19])=O>CN(C)C=O>[CH3:1][C:2]1[C:3]([Cl:19])=[N:4][C:5]([NH:9][C:10]2[S:11][CH:12]=[C:13]([CH3:15])[N:14]=2)=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178431960HCID 178431960, compound

Product 1

HCID 183156854-Chloro-5,6-dimethyl-N-(4-methyl-2-thiazolyl)-2-pyrimidinamineYield 33.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture solution of 5,6-dimethyl-2-(4-methylthiazol-2-yl)amino-4-hydroxypyrimidine (1.15 g, 4-78 mmol), phosphorus oxychioride(7 ml), and dimethylformamide(5 ml) was heated to 70° C. for 30 minutes, cooled to a room temperature and then poured into ice water. The aqueous layer was extracted with dichloromethane, washed with 1N sodium hydroxide solution, and then washed with water. The separated organic layer was concentrated and the residual oil was suspended in a mixture solution of ethyl ether and hexane. The resulting solid was filtered and dried to give 0.42 g of the titled compound. (Yield: 33.9%)

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. washwashed with 1N sodium hydroxide solution
  3. washwashed with water
  4. concentrationThe separated organic layer was concentrated
  5. filtrationThe resulting solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-8d5b275a824a498cbd117255cac1bb98
Source dataset
uspto-grants-2002_03
Patent number
US06352993B1

Reaction notes

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