Chloroacetyl chloride → HCID 66748176, compound

HRID 1464968Notes

Reaction equation

HRID 1464968 reaction equation
Cl.[CH2:2]([O:6][C:7]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[N:10]=[CH:9][N:8]=1)[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.[Cl:26][CH2:27][C:28](Cl)=[O:29]>>[Cl:26][CH2:27][C:28]([N:16]1[CH2:17][CH2:18][N:13]([C:11]2[CH:12]=[C:7]([O:6][CH2:2][CH:3]([CH3:5])[CH3:4])[N:8]=[CH:9][N:10]=2)[CH2:14][CH2:15]1)=[O:29]

Participants

4

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 66748515HCID 66748515, compound

Product 1

HCID 66748176HCID 66748176, compoundYield 86.4%

Procedure

To a mixture of 4-isobutoxy-6-(piperazin-1-yl)pyrimidine hydrochloride (300 mg, 0.97 mmol) and triethylamine (0.68 mL, 4.9 mmol) was added chloroacetyl chloride (121 mg, 1.07 mmol) at 0° C. After being stirred at the same temperature for 30 min, the mixture was poured onto water, and the aqueous layer was extracted with dichloromethane (twice). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (1.5:1-1:1) to give the title compound (262 mg, 86%) as a colorless oil.

Workup

  1. additionthe mixture was poured onto water
  2. extractionthe aqueous layer was extracted with dichloromethane (twice)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (1.5:1-1:1)

Sources & evidence

ORD record
ord-36fd39fffdfd406a9329075232d8acc8
Source dataset
uspto-grants-2015_04
Patent number
US08999974B2

Reaction notes

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