4-(Bromoacetyl)benzonitrile → HCID 178509550, compound

HRID 590623Notes

Reaction equation

HRID 590623 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.CC([O-])=O.[Na+].Br[CH2:16][C:17]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)=O>O.CO>[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[C:5]2[CH:16]=[C:17]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[NH:9][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 517045Sodium AcetateHCID 178507952HCID 178507952, compound

Product 1

HCID 178509550HCID 178509550, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,6-diaminopyrimidin-4-ol (1 g, 7.93 mmol) and NaOAc (0.846 g, 10.31 mmol) in water (180 mL) was heated to 100° C. for 20 minutes. To this was added a suspension of 4-(2-bromoacetyl)benzonitrile (2.2 gm, 8.73 mmol) [prepared according to procedure mentioned in J. Med. Chem., 2011, 54(12), 4042-4056] in MeOH (25 mL) and heated overnight at 100° C. After completion of reaction, the reaction mixture was cooled to 0° C. Resultant solid product was filtered off and dried under reduced pressure to provide title compound XI-10-I (1.2 g, 100%). LCMS: m/z 252 (M+1)+.

Workup

  1. additionTo this was added
  2. temperatureheated overnight at 100° C
  3. customAfter completion of reaction
  4. temperaturethe reaction mixture was cooled to 0° C
  5. filtrationResultant solid product was filtered off
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-08b2a98943b54caa88b7d62f122b570f
Source dataset
uspto-grants-2016_01
Patent number
US09233983B2

Reaction notes

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