Ethanol → 4,6-Dichloro-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine

HRID 1368774Notes

Reaction equation

HRID 1368774 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(O)C.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.P(=O)(O)(O)O>C(Cl)Cl>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1004Phosphoric AcidHCID 754524-Methoxybenzylamine2×HCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 132301344,6-Dichloro-N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 27.5 g portion of 2,4,6-trichloropyrimidine was suspended in a mixed solvent of 200 ml ethanol and 200 ml methylene chloride, to which, under ice-cooling, was subsequently added dropwise 30 ml of 4-methoxybenzylamine. After 19 hours of stirring at the same temperature, 10 ml of 4-methoxybenzylamine was further added dropwise and the mixture was stirred for 18 hours. The reaction solution was mixed with 200 ml of 0.5 N phosphoric acid aqueous solution and extracted with chloroform, and then the organic layer was washed with saturated brine. After drying with anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel chromatography and developed with a chloroform-hexane (3:1) mixed solvent to obtain 13.3 g of 4,6-dichloro-2-(4-methoxybenzyl)aminopyrimidine and further developed with a chloroform-ethyl acetate (1:3) mixed solvent to obtain 24.2 g of 2,6-dichloro-4-(4-methoxybenzyl)aminopyrimidine. 2,6-Dichloro-4-(4-methoxybenzyl)aminopyrimidine

Workup

  1. temperaturecooling
  2. additionwas further added dropwise
  3. extractionextracted with chloroform
  4. washthe organic layer was washed with saturated brine
  5. dry with materialAfter drying with anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. additionmixed solvent

Sources & evidence

ORD record
ord-aecb3be46d584f14a07749a95e25f6e3
Source dataset
uspto-grants-2003_06
Patent number
US06573377B1

Reaction notes

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