Guanidine Hydrochloride → 2-Amino-4-(1-cyclobutyl-2-methylimidazol-5-yl)pyrimidine

HRID 1723660Notes

Reaction equation

HRID 1723660 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[N:11]([CH:12]2[CH2:15][CH2:14][CH2:13]2)[C:10]([CH3:16])=[N:9][CH:8]=1)=O.Cl.[NH2:19][C:20]([NH2:22])=[NH:21].C[O-].[Na+]>C(O)CCC>[NH2:21][C:20]1[N:22]=[C:5]([C:7]2[N:11]([CH:12]3[CH2:13][CH2:14][CH2:15]3)[C:10]([CH3:16])=[N:9][CH:8]=2)[CH:4]=[CH:3][N:19]=1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 67037586HCID 67037586, compound

Product 1

HCID 688800882-Amino-4-(1-cyclobutyl-2-methylimidazol-5-yl)pyrimidineYield 65,640%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-cyclobutyl-2-methylimidazole (Method 37; 466 mg, 2 mmol) and guanidine hydrochloride (476 mg, 5 mmol) were suspended in 1-butanol (10 ml). Sodium methoxide (432 g, 8 mmol) was added in one portion and the mixture heated under reflux, under an atmosphere of nitrogen, for 2 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 97:3) to give the title compound (301 g, 66%). NMR: 1.73 (m, 2H), 2.45 (m, 7H), 5.36 (m, 1H), 6.58 (s, 2H), 6.72 (d, 1H), 7.24 (s, 1H), 8.16 (d, 1H); m/z 230

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux, under an atmosphere of nitrogen, for 2 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 97:3)

Sources & evidence

ORD record
ord-2ca834a520444702aec14e5e16ebcdcf
Source dataset
uspto-grants-2009_02
Patent number
US07485638B2

Reaction notes

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