Lithium Hydroxide → 7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538222Notes

Reaction equation

HRID 538222 reaction equation
[OH-:1].[Li+].[Cl:3][C:4]1[N:9]=[C:8](SC)[N:7]2[CH:12]=[C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[C:6]2[CH:5]=1>O.C1COCC1.C(Cl)Cl>[Cl:3][C:4]1[NH:9][C:8](=[O:1])[N:7]2[CH:12]=[C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:14]=[C:6]2[CH:5]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 866964987-Chloro-5-methylsulfanyl-2-phenoxymethyl-imidazo[1,2-c]pyrimidine

Product 1

HCID 1363786247-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-oneYield 98.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of lithium hydroxide (66 mg, 2.75 mmol) in H2O (10 mL) was added to a solution of 7-chloro-5-methylsulfanyl-2-phenoxymethyl-imidazo[1,2-c]pyrimidine (0.70 g, 2.29 mmol) in THF (10 mL). The mixture was stirred at 50° C. for 4 hours and then diluted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 7-chloro-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (0.62 g, 98% yield) as a white solid that was used in the next step without further purification.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-8e0e01159a9e4dddb29aa7743b138b56
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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