Phosphorus oxychloride → 4-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile

HRID 243536Notes

Reaction equation

HRID 243536 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](O)[N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.P(Cl)(Cl)([Cl:20])=O>>[NH2:1][C:2]1[CH:7]=[C:6]([Cl:20])[N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 178510038HCID 178510038, compound

Product 1

HCID 714650014-((4-Amino-6-chloropyrimidin-2-yl)amino)benzonitrile

Procedure

1900 ml of phosphorus oxychloride was added to a reaction vessel, to this was added 190 g of 4-(4-amino-6-hydroxypyrimidin-2-ylamino)benzonitrile under stirring at RT. The reaction mass was slowly heated to 80-85° C. and maintained at the same temperature for 16-18 hr. After completion of the reaction, phosphorous oxychloride was distilled off and stripped with 950 ml of ethyl acetate. 1900 ml of chilled water was slowly added to the reaction mass and its pH was adjusted to 9-10 with 950 ml of 50% aqueous potassium carbonate. The solid was filtered and dried under vacuum at 55-60° C. overnight.

Workup

  1. temperatureThe reaction mass was slowly heated to 80-85° C.
  2. temperaturemaintained at the same temperature for 16-18 hr
  3. distillationwas distilled off
  4. addition1900 ml of chilled water was slowly added to the reaction mass and its pH
  5. filtrationThe solid was filtered
  6. customdried under vacuum at 55-60° C. overnight

Sources & evidence

ORD record
ord-6630c12d0092488e99dd44f347933f6d
Source dataset
uspto-grants-2014_02
Patent number
US08653266B2

Reaction notes

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