2-Amino-4-chloro-6-methylpyrimidine → 4-Chloro-5-iodo-6-methylpyrimidin-2-amine

HRID 421995Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[I:10]N1C(=O)CCC1=O>C(#N)C.CO>[Cl:8][C:6]1[C:5]([I:10])=[C:4]([CH3:9])[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 2-amino-4-chloro-6-methylpyrimidine (10.0 g, 70.0 mmol) in acetonitrile (100 mL) and MeOH (140 mL) was added N-iodosuccinimide (24.0 g, 105.0 mmol) at room temperature. The reaction was heated to 60° C. and stirred for 5 h under nitrogen and was then cooled to room temperature. About 80% of the solvent was evaporated under reduced pressure and the mixture was diluted with diethyl ether (200 mL) to afford 4-chloro-5-iodo-6-methylpyrimidin-2-amine as a fine crystal (yield: 15.70 g, 83.2%). LC/MS: calculated for C5H5 ClN3 (270.47). found: 272.65 (M+2). HPLC analytical purity: 97.3%.

Workup

temperaturewas then cooled to room temperature
customAbout 80% of the solvent was evaporated under reduced pressure
additionthe mixture was diluted with diethyl ether (200 mL)

Sources & evidence

ORD record: ord-fbca27410786445b924713e2eadd03c1
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101622B2

Reaction notes

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