Chloroacetyl chloride → HCID 67030278, compound

HRID 2192344Notes

Reaction equation

HRID 2192344 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][N:8]=1.CCN(CC)CC>C(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][N:8]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 689584-Aminopyrimidine

Product 1

HCID 67030278HCID 67030278, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of chloroacetyl chloride (1.22 mmol) in anhydrous CHCl3 (2.4 mL) was added slowly to a mixture of 4-aminopyrimidine (1.11 mmol) and Et3N (1.66 mmol) in anhydrous CHCl3 (22 mL) at room temperature. The bright yellow mixture gradually turned orange and after 4 hr the reaction was quenched with H2O (1 mL). After stirring for 15 min the mixture was concentrated to dryness under reduced pressure and the residue purified by flash silica gel chromatography (1-2% MeOH/dichloromethane) to give a yellow solid (122 mg).

Workup

  1. customThe bright yellow mixture gradually turned orange and after 4 hr the reaction was quenched with H2O (1 mL)
  2. concentrationwas concentrated to dryness under reduced pressure
  3. customthe residue purified by flash silica gel chromatography (1-2% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-04276d6070f2444ea56ab3ca172f0c65
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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