Hydrochloric Acid → 3-[4-Bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-2,5-dimethyl-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine, hydrochloride

HRID 1660743Notes

Reaction equation

HRID 1660743 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:25]2[N:26]([CH3:30])[N:27]=[CH:28][N:29]=2)[S:5][C:6]=1[C:7]1[C:8]([CH3:24])=[N:9][N:10]2[C:15]([CH:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[CH:14][C:13]([CH3:23])=[N:12][C:11]=12.[ClH:31].C(OCC)C>CC(C)=O>[ClH:31].[Br:1][C:2]1[N:3]=[C:4]([C:25]2[N:26]([CH3:30])[N:27]=[CH:28][N:29]=2)[S:5][C:6]=1[C:7]1[C:8]([CH3:24])=[N:9][N:10]2[C:15]([CH:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[CH:14][C:13]([CH3:23])=[N:12][C:11]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 247588853-[4-Bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-2,5-dimethyl-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 1317292063-[4-Bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-2,5-dimethyl-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine, hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 3-[4-bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-2,5-dimethyl-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine (750 mg, 1.54 mmol) in acetone (5 mL) and add 1 M HCl in diethyl ether (1.84 mL, 1.84 mmol). Stir the mixture at room temperature for 3 h and concentrate in vacuo. Dissolve the residue in diethyl ether/hexane=1/1 (5 mL) and crystallize the desired HCl salt (526 mg, 65%). ES/MS m/z (81Br) 490 (M+1)+; 1H-NMR(CDCl3): 8.20 (s, 1H), 6.82 (s, 1H), 4.21 (s, 3H), 3.64 (m, 1H), 2.49 (m, 3H), 2.44 (s, 3H), 1.75 (m, 4H), 1.96(m, 4H), 0.81 (m, 6H).

Workup

  1. concentrationconcentrate in vacuo
  2. dissolutionDissolve the residue in diethyl ether/hexane=1/1 (5 mL)
  3. customcrystallize the desired HCl salt (526 mg, 65%)

Sources & evidence

ORD record
ord-a5eb7ffec9214d90a4929845c6effbb2
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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