Hydrochloric Acid → (S)-2-chloro-5-(2-(pyrrolidin-2-yl)-1H-imidazol-5-yl)pyrimidine trihydrochloride

HRID 237917Notes

Reaction equation

HRID 237917 reaction equation
[ClH:1].[Cl:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C@@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3C(OC(C)(C)C)=O)=[N:11][CH:10]=2)=[CH:5][N:4]=1>CO>[ClH:2].[ClH:1].[ClH:2].[Cl:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C@@H:14]3[CH2:18][CH2:17][CH2:16][NH:15]3)=[N:11][CH:10]=2)=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57462161(S)-tert-butyl 2-(5-(2-chloropyrimidin-5-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86618479(S)-2-chloro-5-(2-(pyrrolidin-2-yl)-1H-imidazol-5-yl)pyrimidine trihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cold (0° C.) 4 N HCl in dioxanes (5 mL) was added via syringe to (S)-tert-butyl 2-(5-(2-chloropyrimidin-5-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (152d-1, 0.50 g, 1.43 mmol) in a 100 mL pear-shaped flask followed by MeOH (1.0 mL). The suspension was stirred at room temperature for 4 h before it was concentrated down to dryness and placed under high vacuum for 1 h. There was isolated intermediate (S)-2-chloro-5-(2-(pyrrolidin-2-yl)-1H-imidazol-5-yl)pyrimidine trihydrochloride as a pale yellow solid (with an orange tint) which was used without further purification.

Workup

  1. concentrationwas concentrated down to dryness
  2. waitplaced under high vacuum for 1 h

Sources & evidence

ORD record
ord-0d3db05d220042cdbf5f23e65dd3d2bf
Source dataset
uspto-grants-2014_02
Patent number
US08642025B2

Reaction notes

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