Potassium Carbonate → HCID 117942033, compound

HRID 1499274Notes

Reaction equation

HRID 1499274 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[Cl:11][C:12]1[CH:17]=[C:16](CCl)[N:15]=[C:14]([NH2:20])[N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][O:10][C:16]1[CH:17]=[C:12]([Cl:11])[N:13]=[C:14]([NH2:20])[N:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 201534884-Chloro-6-(chloromethyl)pyrimidin-2-amineHCID 54049764(2-Bromo-4-chlorophenyl)methanol

Product 1

HCID 117942033HCID 117942033, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (2-bromo-4-chlorophenyl)methanol (173 mg, 1. mmol), 4-chloro-6-(chloromethyl)pyrimidin-2-amine (178 mg, 1.16 mmol) and K2CO3 (175 mg, 1.00 mmol) in DMF (5 mL) was heated to 100° C. for 12 h. The reaction was cooled to RT, concentrated in vacuo, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification on normal phase silica gel (EtOAc/petroleum ether) provided 4-((2-bromo-4-chlorobenzyl)oxy)-6-chloropyrimidin-2-amine as a white solid.

Workup

  1. temperatureThe reaction was cooled to RT
  2. concentrationconcentrated in vacuo
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customPurification on normal phase silica gel (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-e2262ef03df541cf904756d96888e643
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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