Phosphorus oxychloride → 4-Chloro-2-cyclopropylpyrimidine

HRID 386110Notes

Reaction equation

HRID 386110 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8](O)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1785164792-Cyclopropylpyrimidin-4-ol

Product 1

HCID 249037134-Chloro-2-cyclopropylpyrimidine

Procedure

2-Cyclopropylpyrimidin-4-ol (1.0 g, 7.34 mmol) was suspended in phosphorous oxychloride (5.0 mL, 53.6 mmol) and over the course of about one hour, the solid went into solution. After three hours, the solution was concentrated, diluted with ethyl acetate, washed with saturated sodium bicarbonate, water, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate, water, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9c8f72b7d4164b498201963607698ca7
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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