Phenol → 7-Chloro-5-methylsulfanyl-2-phenoxymethyl-imidazo[1,2-c]pyrimidine

HRID 538221Notes

Reaction equation

HRID 538221 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:8][C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]2[CH:17]=[C:18]([CH2:20]Cl)[N:19]=[C:11]2[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:8][C:9]1[N:14]=[C:13]([S:15][CH3:16])[N:12]2[CH:17]=[C:18]([CH2:20][O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:19]=[C:11]2[CH:10]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 592992327-Chloro-2-(chloromethyl)-5-methylsulfanyl-imidazo[1,2-c]pyrimidine

Product 1

HCID 866964987-Chloro-5-methylsulfanyl-2-phenoxymethyl-imidazo[1,2-c]pyrimidineYield 53%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Phenol (0.050 g, 0.53 mmol) was added to a suspension of 7-chloro-2-chloromethyl-5-methylsulfanyl-imidazo[1,2-c]pyrimidine (0.15 g, 0.53 mmol) and K2CO3 (0.21 g, 1.58 mmol) in ACN (2 mL). The mixture was stirred at 50° C. for 18 hours and then the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with diethyl ether and the solid thus obtained, filtered and dried in vacuo to yield 7-chloro-5-methylsulfanyl-2-phenoxymethyl-imidazo[1,2-c]pyrimidine (0.085 g, 53% yield) as a white solid.

Workup

  1. customthe solvents were evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica; DCM)
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo
  5. customThe product was triturated with diethyl ether
  6. customthe solid thus obtained
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-e2be81f82a4c4ba79a576559d3cb73e0
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

Loading…