Hydrochloric Acid → 7-Chloromethylimidazo[1,2-alpha]pyrimidine hydrochloride

HRID 1796100Notes

Reaction equation

HRID 1796100 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10]O)=[N:6][C:5]=12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.[ClH:36]>ClCCl>[ClH:36].[Cl:36][CH2:10][C:7]1[CH:8]=[CH:9][N:4]2[CH:3]=[CH:2][N:1]=[C:5]2[N:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 18001293Imidazo[1,2-a]pyrimidin-7-ylmethanol

Product 1

HCID 695607647-Chloromethylimidazo[1,2-alpha]pyrimidine hydrochlorideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of imidazo[1,2-α]pyrimidin-7-ylmethanol (4.64 g, 34.1 mmol) in dichloromethane under an atmosphere of nitrogen was added triphenylphosphine (10.6 g, 40.5 mmol) and carbon tetrabromide (13.4 g, 40.5 mmol). This mixture was stirred at room temperature for 2.5 h before addition of ethereal hydrogen chloride (1.0M, 100 ml) in a dropwise manner and allowed to stir at room temperature for a further 1 h. Reaction mixture was evaporated to dryness under reduced pressure and the resulting solid washed with dichloromethane followed by ether and then dried under vacuum to give 7-chloromethylimidazo[1,2-α]pyrimidine hydrochloride salt (5.0 g, 79%) as a pale brown solid: δH (360 MHz, d6-DMSO) 5.06 (2H, s), 7.77 (1H, d, J 7), 8.31-8.35 (2H, m), 9.37 (1H, d, J 7); m/z (ES+) 168, 170 (M++H).

Workup

  1. customReaction mixture
  2. customwas evaporated to dryness under reduced pressure
  3. washthe resulting solid washed with dichloromethane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1effa26c71ed41f9a4c44508a890591f
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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