Phosphorus oxychloride → 4-Chloro-2-cyclohexyl-5,6-dimethylpyrimidine

HRID 1182738Notes

Reaction equation

HRID 1182738 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH:6]1([C:12]2[N:17]=[C:16](O)[C:15]([CH3:19])=[C:14]([CH3:20])[N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>>[Cl:3][C:16]1[C:15]([CH3:19])=[C:14]([CH3:20])[N:13]=[C:12]([CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[N:17]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432490HCID 178432490, compound

Product 1

HCID 581142624-Chloro-2-cyclohexyl-5,6-dimethylpyrimidine

Procedure

POCl3 (220 ml, 2.4 mol, ˜26 eq) was cooled to ˜−50° C. before being carefully treated with 2-cyclohexyl-5,6-dimethylpyrimidin-4-ol (28.9 g, ‘92 mmol’, 1 eq). The cooling bath was then removed and the pot allowed to warm to RT followed by heating to reflux for 6 h. The RM was concentrated, treated with ice and saturated NaHCO3 and extracted into Et2O before being dried (sodium sulfate)/concentrated. The resulting oil was subjected to column chromatography using EtOAc (10%): 40-60 Petrols (90%) as eluent to yield 4-chloro-2-cyclohexyl-5,6-dimethylpyrimidine as an oil (5.7011 g, 28% over first two steps). 1H (400 MHz, DMSO) 1.16-1.90 (10H, m), 2.26 (3H, s), 2.46 (3H, s), 2.60-2.75 (1H, m). ES+225.

Workup

  1. customThe cooling bath was then removed
  2. temperatureby heating
  3. temperatureto reflux for 6 h
  4. concentrationThe RM was concentrated
  5. additiontreated with ice and saturated NaHCO3
  6. extractionextracted into Et2O
  7. dry with materialbefore being dried (sodium sulfate
  8. concentration)/concentrated

Sources & evidence

ORD record
ord-1f33caf77f8d4838bfc5943794652e58
Source dataset
uspto-grants-2014_03
Patent number
US08664219B2

Reaction notes

Loading…