Guanidine Hydrochloride → 2-Amino-4-(1,2-dimethylimidazol-5-yl)pyrimidine

HRID 1064328Notes

Reaction equation

HRID 1064328 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH3:12])[C:10]([CH3:13])=[N:9][CH:8]=1)=O.Cl.[NH2:16][C:17]([NH2:19])=[NH:18].C[O-].[Na+]>C(O)CCC>[NH2:18][C:17]1[N:19]=[C:5]([C:7]2[N:11]([CH3:12])[C:10]([CH3:13])=[N:9][CH:8]=2)[CH:4]=[CH:3][N:16]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 693105495-(3-Dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazole

Product 1

HCID 222735092-Amino-4-(1,2-dimethylimidazol-5-yl)pyrimidineYield 84%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1,2-dimethylimidazole (Method 15; 2.8 g, 14.5 mmol) and guanidine hydrochloride (3.5 g, 36.3 mmol) were suspended in 1-butanol (30 ml). Sodium methoxide (3.1 g, 58 mmol) was added in one portion and the mixture heated under reflux, under an atmosphere of nitrogen, for 18 hours. The reaction mixture was allowed to cool to ambient temperature and was pre-absorbed on to silica gel and purified by column chromatography on silica gel eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 95:5) to give the title compound (2.3 g, 84%). NMR 2.16 (s, 3H), 3.93 (s, 3H) 6.52 (s, 2H), 6.80 (d, 1H), 7.47 (s, 1H), 8.17 (d, 1H); m/z 190.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux, under an atmosphere of nitrogen, for 18 hours
  3. customwas pre-absorbed on to silica gel
  4. custompurified by column chromatography on silica gel eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 95:5)

Sources & evidence

ORD record
ord-29b34fde1e434d158be0135e85994a0b
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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