Ammonia → HCID 58550500, compound

HRID 1891003Notes

Reaction equation

HRID 1891003 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:17]=[CH:16][NH:15][C:14](=O)[CH:13]=1.N.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:14]1[CH:13]=[C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][O:2][CH3:1])[N:17]=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 1361275736-[2-(2-methoxy-ethoxy)-phenyl]3H-pyrimidin-4-one

Product 1

HCID 58550500HCID 58550500, compound

Conditions

Temperature
5 °C

Procedure

A stirred suspension of 6-[2-(2-methoxy-ethoxy)-phenyl]-3H-pyrimidin-4-one (0.2 g, 0.81 mmol) in POCl3 (2 mL) was heated at reflux for 1 h. The reaction mixture was cooled to about 5° C. and poured cautiously into 10 ml ice-water, ammonia (10 mL) was added and extracted with ethyl acetate (2×10 mL), organic layers were combined, washed with water (5 mL) then dried over anhydrous sodium sulfate and concentrated. The residue was triturated with hexane yielding 0.18 g (84%) 4-chloro-6-[2-(2-methoxy-ethoxy)-phenyl]-pyrimidine as white powder.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. additionwas added
  4. extractionextracted with ethyl acetate (2×10 mL), organic layers
  5. washwashed with water (5 mL)
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was triturated with hexane yielding 0.18 g (84%) 4-chloro-6-[2-(2-methoxy-ethoxy)-phenyl]-pyrimidine as white powder

Sources & evidence

ORD record
ord-b199597bf0764f4982cdf425715168fe
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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