Hydrochloric Acid → 2-(1H-Imidazol-2-yl)pyrimidine

HRID 44818

Reaction equation

HRID 44818 reaction equation
O(C)[Na].[N:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[C:10]#[N:11].CO[CH:14](OC)[CH2:15][NH2:16].Cl.C([O-])([O-])=O.[Na+].[Na+]>CO.CC(O)=O>[NH:11]1[CH:14]=[CH:15][N:16]=[C:10]1[C:5]1[N:6]=[CH:7][CH:8]=[CH:9][N:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 89728Aminoacetaldehyde dimethyl acetalHCID 27579792-CyanopyrimidineHCID 178418582HCID 178418582, compound

Product 1

HCID 222603812-(1H-Imidazol-2-yl)pyrimidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of NaOCH3 (270 mg) in 50 mL of MeOH, pyrimidine-2-carbonitrile (1-Im-3, 50 mmol) was added. The mixture was stirred at rt for 1 h, then 2,2-dimethoxyethanamine (50 mmol) was added followed by 2 mL of AcOH. This mixture was stirred for 1 h, then 6N HCl was added to adjust pH=1. The resulting acidic solution was heated at reflux for 18 h. After cooling to rt, the reaction was poured into a mixture of ice and aqueous Na2CO3 solution, then extracted with EtOAc and the organic layer was concentrated to give 2-(1H-imidazol-2-yl)pyrimidine (Imidazole 3). LCMS (0.01% Ammonia): 147.2 m/z (M+H)+; 1H-NMR (DMSO-d6, 500 MHz): δ: 13.04 (bs, 1H), 8.87 (d, 2H, J=5.0 Hz), 7.44 (t, 1H, J=5.0 Hz), 7.24 (s, 2H).

Workup

  1. stirringThis mixture was stirred for 1 h
  2. temperatureThe resulting acidic solution was heated
  3. temperatureat reflux for 18 h
  4. temperatureAfter cooling to rt
  5. extractionextracted with EtOAc
  6. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-3efa941e35b743f19d799349cdbadad5
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

Loading…