Diiodomethane → 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

HRID 629487Notes

Reaction equation

HRID 629487 reaction equation
[CH:1]([N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=2)[C:6](N)=[N:5]1)([CH3:3])[CH3:2].C(ON=O)CC(C)C.C(I)[I:27]>>[I:27][C:6]1[C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([S:15][CH3:16])[N:10]=2)=[CH:8][N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 510342271-isopropyl-4-(2-(methylthio)pyrimidin-4-yl)-1H-pyrazol-3-amine

Product 1

HCID 594244094-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)-2-(methylthio)pyrimidine

Conditions

Temperature
100 °C

Procedure

A mixture of Intermediate 1-isopropyl-4-(2-(methylthio)pyrimidin-4-yl)-1H-pyrazol-3-amine (4.0 g, 16.0 mmol), isopentylnitrite (13.2 g, 112 mmol), and methylene iodide (30 mL) was heated at 100° C. for 3 h. Removal of the volatiles under vacuum provided a dark residue, which was purified by silica gel chromatography (2:1 hexane/ethyl acetate eluant) to afford the title compound as a solid; MS m/z: 361.1 (M+1).

Workup

  1. customRemoval of the volatiles under vacuum
  2. customprovided a dark residue, which
  3. customwas purified by silica gel chromatography (2:1 hexane/ethyl acetate eluant)

Sources & evidence

ORD record
ord-d3427ae677ba4ac8b23a654b79dc9c42
Source dataset
uspto-grants-2016_04
Patent number
US09314464B2

Reaction notes

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