Water → HCID 66652755, compound

HRID 2283635Notes

Reaction equation

HRID 2283635 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].C(N(CC)CC)C.O>C(O)C>[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH2:13][NH:14][C:2]1[N:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5834662-Chloro-5-fluoropyrimidineHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 66652755HCID 66652755, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2-Chloro-5-fluoropyrimidine (4.05 g, 30.6 mmol), 2,4-dimethoxybenzylamine (5.0 mL, 31 mmol) and triethylamine (3.72 g, 36.7 mmol) were stirred in ethanol (200 mL) and heated at 50° C. for 48 hours. The cooled reaction mixture was poured into water and extracted with ethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexanes to ethyl acetate gradient elution) then triturated with ethyl ether:hexanes. The solid was collected by filtration and dried in vacuo to afford the title compound as a white solid (4.16 g).

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl ether (×2)
  3. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexanes to ethyl acetate gradient elution)
  6. customthen triturated with ethyl ether
  7. filtrationThe solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f0bfa0565a5b4575b4fddae5e0c4ef74
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

Loading…