(S)-tert-butyl 2-(5-(2-chloropyrimidin-5-yl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate → (S)-2-chloro-5-(2-(pyrrolidin-2-yl)-1H-imidazol-5-yl)pyrimidine trihydrochloride

HRID 453971Notes

Reaction equation

HRID 453971 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][N:14]3C(OC(C)(C)C)=O)=[N:10][CH:9]=2)=[CH:4][N:3]=1>CO>[ClH:1].[ClH:1].[ClH:1].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C@@H:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)=[N:10][CH:9]=2)=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 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 NHCl 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-ce5a71a2b8834713a0a65e14e6f186d7
Source dataset
uspto-grants-2013_07
Patent number
US08492553B2

Reaction notes

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