Ammonia → (RS)-S-{4-[(5-bromo-4-chloropyrimidin-2-yl)amino]phenyl}-S-methyl sulfoximide

HRID 1391468Notes

Reaction equation

HRID 1391468 reaction equation
[Br:1][C:2]1[C:3](O)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.N.P(Cl)(Cl)([Cl:23])=O>>[Br:1][C:2]1[C:3]([Cl:23])=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[NH:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178504584HCID 178504584, compound

Product 1

HCID 59674032(RS)-S-{4-[(5-bromo-4-chloropyrimidin-2-yl)amino]phenyl}-S-methyl sulfoximide

Conditions

Temperature
106 °C

Procedure

255 mg of (RS)-S-{4-[(5-bromo-4-hydroxypyrimidin-2-yl)amino]phenyl}-S-methyl sulfoximide is suspended in 1.5 ml of phosphorus oxychloride and stirred for 3 hours at 106° C. and for 16 hours at room temperature. The mixture is poured into ice water, made alkaline with 25% ammonia solution while being cooled intensely (temperature <5° C.) and stirred for 1 hour in an ice bath. The precipitate is suctioned off, washed with water and dried at 60° C. 220 mg (81.8% of theory) of the product with a melting point of 170-173° C. is obtained.

Workup

  1. temperaturewhile being cooled intensely (temperature <5° C.)
  2. stirringstirred for 1 hour in an ice bath
  3. washwashed with water
  4. customdried at 60° C
  5. custom220 mg (81.8% of theory) of the product with a melting point of 170-173° C. is obtained

Sources & evidence

ORD record
ord-19500b27f02a4ffaa1d81119156d1c75
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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