Phosphorus oxychloride → 2-Chloro-4-(3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl)pyrimidine

HRID 1889239Notes

Reaction equation

HRID 1889239 reaction equation
[I:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[C:9](O)[N:8]=2)=[CH:5][N:4]([CH:14]([CH3:16])[CH3:15])[N:3]=1.P(Cl)(Cl)([Cl:19])=O>>[Cl:19][C:9]1[N:8]=[C:7]([C:6]2[C:2]([I:1])=[N:3][N:4]([CH:14]([CH3:16])[CH3:15])[CH:5]=2)[CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178456194HCID 178456194, compound

Product 1

HCID 510343412-Chloro-4-(3-iodo-1-(1-methylethyl)-1H-pyrazol-4-yl)pyrimidine

Procedure

A solution of Intermediate 4-(3-iodo-1-isopropyl-1H-pyrazol-4-yl)pyrimidin-2-ol (438 mg, 1.33 mmol) in phosphorous oxychloride (10 ml) was heated at 110° C. for 16 h. The mixture was concentrated under vacuum, then aqueous sodium bicarbonate solution was carefully added and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to provide the title compound as a yellow solid. MS m/z 349.0 (M+1).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionaqueous sodium bicarbonate solution was carefully added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-58380930de8348979445d2f41c668b9e
Source dataset
uspto-grants-2013_08
Patent number
US08501758B2

Reaction notes

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