Hydrochloric Acid → methyl 5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate hydrochloride

HRID 1853050Notes

Reaction equation

HRID 1853050 reaction equation
C[Si](C)(C)CCOC[N:7]1[CH:11]=[C:10]([C:12]2[N:17]3[CH:18]=[CH:19][N:20]=[C:16]3[CH:15]=[C:14]([C:21]([O:23][CH3:24])=[O:22])[N:13]=2)[CH:9]=[N:8]1.C(Cl)[Cl:28].Cl.O1CCOCC1>>[ClH:28].[NH:7]1[CH:11]=[C:10]([C:12]2[N:17]3[CH:18]=[CH:19][N:20]=[C:16]3[CH:15]=[C:14]([C:21]([O:23][CH3:24])=[O:22])[N:13]=2)[CH:9]=[N:8]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 67456583methyl 5-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate

Product 1

HCID 86685326methyl 5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate hydrochlorideYield 101.4%

Procedure

In a 100 mL flask, methyl 5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate (0.477 g, 1.28 mmol) (Example 45; Step C) was dissolved in DCM (12.8 mL, 1.28 mmol). To this was added 4N HCl in dioxane (4.79 mL, 19.2 mmol). After stirring at ambient temperature for 4 hours, the reaction mixture was concentrated down to remove solvents. The resultant solid was diluted in DCM, sonicated and filtered to afford 0.363 g (100% yield) of the HCl salt as a light yellow solid. MS (apci) m/z=244.3 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated down
  2. customto remove solvents
  3. additionThe resultant solid was diluted in DCM
  4. customsonicated
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1cbd8bd0719143909365150d7e7e8546
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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