Chlorosuccinimide → 2-Amino-4-(1,2-dimethylimidazol-5-yl)-5-chloropyrimidine

HRID 1064347Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH3:14])=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:15]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH3:14])=[N:10][CH:9]=2)[C:5]([Cl:15])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

2-Amino-4-(1,2-dimethylimidazol-5-yl)pyrimidine (Method 26; 378 mg, 2 mmol) and N-chlorosuccimide (267 mg, 2 mmol) were dissolved in glacial acetic acid (7 ml) under an atmosphere of nitrogen. The reaction mixture was heated at 65° C. for 18 hours when further N-chlorosuccinimide (89 mg, 0.66 mmol) was added and the reaction heated at 65° C. for an additional 2 hours. The volatiles were removed by evaporation and the residue dissolved in water (10 ml). The solution was adjusted to pH 11-12 by addition of 40% aqueous sodium hydroxide solution. The precipitated solid was collected by filtration and washed sparingly with water, dried under vacuum at 60° C. to give the title compound (344 mg, 77%) as a yellow solid. NMR 2.35 (s, 3H, 3.75 (s, 3H), 4.83 (s, 2H), 7.53 (s, 1H), 8.27 (s, 1H); m/z 224.

Workup

additionwas added
customThe volatiles were removed by evaporation
dissolutionthe residue dissolved in water (10 ml)
additionThe solution was adjusted to pH 11-12 by addition of 40% aqueous sodium hydroxide solution
filtrationThe precipitated solid was collected by filtration
washwashed sparingly with water
customdried under vacuum at 60° C.

Sources & evidence

ORD record: ord-acab7ec0e0684739985ff5a03ff4bc82
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969714B2

Reaction notes

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