Ammonia → 6-(4-Chloro-1H-imidazol-1-yl)-4-pyrimidinamine

HRID 1876046Notes

Reaction equation

HRID 1876046 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([Cl:13])[N:10]=[CH:9]2)[N:5]=[CH:4][N:3]=1.[NH3:14]>C(O)(C)C>[Cl:13][C:11]1[N:10]=[CH:9][N:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH2:14])[CH:7]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 592865734-chloro-6-(4-chloro-1H-imidazol-1-yl)pyrimidine

Product 1

HCID 592865626-(4-Chloro-1H-imidazol-1-yl)-4-pyrimidinamineYield 98.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloro-6-(4-chloro-1H-imidazol-1-yl)pyrimidine (0.99 g, 4.60 mmol) in 2 M ammonia (20 mL, 40.0 mmol)/isopropanol was heated at 80° C. in a sealed vial for 18 h. After cooling the solid precipitate was filtered and dried to give 6-(4-chloro-1H-imidazol-1-yl)pyrimidin-4-amine (884 mg, 98% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.44 (1H, d, J=1.51 Hz), 8.32 (1H, d, J=0.76 Hz), 7.96 (1H, d, J=1.51 Hz), 7.30 (2H, br. s.), 6.58 (1H, d, J=1.01 Hz). LCMS: RT=0.57 min, MH+=196.1.

Workup

  1. temperatureAfter cooling the solid precipitate
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-10c75d0465b249a097deb98ce985e784
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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