Diiodomethane → 2-Iodo-6-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine

HRID 1859395Notes

Reaction equation

HRID 1859395 reaction equation
N[C:2]1[N:7]=[C:6]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([CH3:19])=[CH:4][N:3]=1.C(ON=O)CC(C)C.[I:28]CI>>[I:28][C:2]1[N:3]=[CH:4][C:5]([CH3:19])=[C:6]([O:8][C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:7]=1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 120567112-Amino-4-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine

Product 1

HCID 120567122-Iodo-6-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine

Conditions

Temperature
90 °C

Procedure

To a suspension of 2-amino-4-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-5-methylpyrimidine (5 g) in diiodomethane (25 ml) is added isopentylnitrite (48 ml) and the mixture is heated to 90° C. for 30 min. After cooling, the brownish reaction mixture is evaporated in vacuo and the residue is purified by silica-gel flash chromatography. One obtains the title compound as crystals of mp. 94° C.

Workup

  1. temperatureAfter cooling
  2. customthe brownish reaction mixture
  3. customis evaporated in vacuo
  4. customthe residue is purified by silica-gel flash chromatography

Sources & evidence

ORD record
ord-01a22e4a8afd45d9a3bed6276b410b47
Source dataset
uspto-grants-2003_03
Patent number
US06528456B2

Reaction notes

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