5-Amino-4,6-dichloropyrimidine → 2-(2,6-Dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide

HRID 60186

Reaction equation

HRID 60186 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10](Cl)=[O:11].[Cl:13][C:14]1[C:19]([NH2:20])=[C:18]([Cl:21])[N:17]=[CH:16][N:15]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:20][C:19]1[C:14]([Cl:13])=[N:15][CH:16]=[N:17][C:18]=1[Cl:21])=[O:11]

Participants

3

Reactant 2

HCID 794345-Amino-4,6-dichloropyrimidineHCID 27581482-(2,6-Dichlorophenyl)acetyl chloride

Product 1

HCID 577424622-(2,6-Dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamideYield 84%

Conditions

Temperature
130 °C

Procedure

To a mixture of 2,6-dichlorophenyl acetic acid (100 g, 487 mmol) and DMF (1.5 mL) in toluene (600 mL) was added thionyl chloride (116 g, 974 mmol). The resulting mixture was stirred at rt. After 12 h, the solution was concentrated to provide 2,6-dichloro-phenylacetyl chloride as colorless oil. MS (ESI): mass calcd. for C8H5Cl3O, 221.94; m/z found, 223.0 [M+H]+. 1H NMR (CDCl3): 7.33 (d, J=8.1 Hz, 2H), 7.29-7.24 (m, 1H), 4.56 (s, 2H). A suspension of the crude 2,6-dichloro-phenylacetyl chloride and 4,6-dichloro-pyrimidin-5-ylamine (76 g, 463 mmol) was heated neat to 130° C. After 1 h, the resulting solid was cooled, collected by filtration, and washed with cold MeOH (400 mL) to provide the title compound as a solid (135 g, 84%). MS (ESI): mass calcd. for C12H7Cl4N3O, 348.9; m/z found, 350.0 [M+H]+. 1H NMR ((CD3)2SO): 10.59 (s, 1H), 8.86 (s, 1H), 7.50 (d, J=8.0 Hz, 2H), 7.37-7.33 (m, 1H), 4.13 (s, 2H).

Workup

  1. temperaturethe resulting solid was cooled
  2. filtrationcollected by filtration
  3. washwashed with cold MeOH (400 mL)

Sources & evidence

ORD record
ord-c7b21a5e8ac0419682285e24ce26acfd
Source dataset
uspto-grants-2016_09
Patent number
US09440978B2

Linked notes

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