Hydrochloric Acid → HCID 67457657, compound

HRID 1852965Notes

Reaction equation

HRID 1852965 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12](SCC)[N:11]3[CH:17]=[CH:18][N:19]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.C[OH:21].[OH-].[K+].Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:21])[N:11]3[CH:17]=[CH:18][N:19]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 67458003HCID 67458003, compound

Product 1

HCID 67457657HCID 67457657, compoundYield 94.71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a flask charged with 7-(4-bromophenyl)-5-(ethylthio)imidazo[1,2-c]pyrimidine (62.34 g, 186.5 mmol), methanol (250 mL), and potassium hydroxide (52.32 g, 932.6 mmol) was added water (250 mL) and the reaction was fitted with a condenser and heated to reflux for 4 hours. The reaction mixture was diluted with water (500 mL) and acidified with concentrated hydrochloric acid to a pH=5. The solids were collected by vacuum filtration and then washed with water (3×500 mL) and the cake was dried. The semi dry solids were placed in a vacuum desiccator under high vacuum for two days to afford 7-(4-bromophenyl)imidazo[1,2-c]pyrimidin-5(6H)-one (51.25 g, 176.7 mmol, 94.71% yield). MS (apci) m/z=290.0 (M+H).

Workup

  1. customthe reaction was fitted with a condenser
  2. temperatureheated
  3. temperatureto reflux for 4 hours
  4. filtrationThe solids were collected by vacuum filtration
  5. washwashed with water (3×500 mL)
  6. customthe cake was dried
  7. customThe semi dry solids

Sources & evidence

ORD record
ord-b815d4fedd8e4218ba13f0fdeedb1608
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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