Chloroacetyl chloride → HCID 68283152, compound

HRID 624029Notes

Reaction equation

HRID 624029 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([NH2:11])[N:4]=1.CCN(C(C)C)C(C)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl>[Cl:21][CH2:22][C:23]([NH:11][C:5]1[N:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][N:6]=1)=[O:24]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 129881044,5-Dimethoxypyrimidin-2-amine

Product 1

HCID 68283152HCID 68283152, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,5-dimethoxypyrimidin-2-amine (350 mg, 2.26 mmol) in DCM (3.5 mL), DIPEA (1.2 mL, 7.0 mmol) was added, followed by chloracetylchloride (0.30 mL, 3.72 mmol). The resulting dark brown reaction mixture was stirred at rt for 1 h, then quenched with water and diluted with DCM. The org. layer was separated and the aq. layer extracted with DCM (1×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent removed under reduced pressure to obtain 2-chloro-N-(4,5-dimethoxypyrimidin-2-yl)acetamide as a brown oil which was used in the next step without further purification. LC-MS conditions B: tR=0.38 min, [M+H]+=232.07.

Workup

  1. customquenched with water
  2. additiondiluted with DCM
  3. customlayer was separated
  4. extractionthe aq. layer extracted with DCM (1×)
  5. washlayers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d05eb4b1be0a4428a98ffc64274d35bb
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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