Phosphorus oxychloride → 4-Chloro-6-(methoxymethyl)pyrimidine

HRID 1241400Notes

Reaction equation

HRID 1241400 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6](O)[CH:5]=1.O=P(Cl)(Cl)[Cl:13]>C(Cl)Cl>[Cl:13][C:6]1[CH:5]=[C:4]([CH2:3][O:2][CH3:1])[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178494553HCID 178494553, compound

Product 1

HCID 143061714-Chloro-6-(methoxymethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(Methoxymethyl)pyrimidin-4-ol (948 mg, 6.8 mmole) was taken up in CH2Cl2 (10 mL) and POCl3 (6 mL) at room temperature. After 18 hours, the mixture was concentrated to dryness. The residue was taken up in ice water and the pH adjusted to 7. The mixture was extracted with CHCl3 (4×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the title compound which was sufficiently pure for use in the next step without purification. 1H-NMR (500 MHz, CDCl3) δ 8.95 (s, 1H), 7.58 (s, 1H), 4.48 (s, 2H), 3.50 (s, 3H).

Workup

  1. customat room temperature
  2. concentrationthe mixture was concentrated to dryness
  3. extractionThe mixture was extracted with CHCl3 (4×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16dc8b5abd4b4bd3a3d76b1a851a99e0
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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