Chloroform → HCID 57428967, compound

HRID 2281660Notes

Reaction equation

HRID 2281660 reaction equation
Cl[C:2]1[C:3]2[CH:11]=[C:10]([CH3:12])[O:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[O:13]=P(Cl)(Cl)Cl.C(Cl)(Cl)Cl.CCCCCC>C(OC(=O)C)(=O)C>[CH3:8][C:6]1[NH:7][C:2](=[O:13])[C:3]2[CH:11]=[C:10]([CH3:12])[O:9][C:4]=2[N:5]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8058Hexane2×HCID 24813Phosphorus oxychlorideHCID 57428968HCID 57428968, compound

Product 1

HCID 57428967HCID 57428967, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

4-Chloro-2,6-dimethylfuro[2,3-d]pyrimidine (M).To a 50 mL flask was added 1.64 g (1 mmol) L and 10 mL POCl3. The resulting mixture was refluxed for 2 h, and the solvent was removed under reduced pressure to afford a dark residue. To this was added 30 mL of CHCl3 and 3 g of silica gel. The solvent was evaporated to afford a plug. Column chromatography of the plug with hexane:acetyl acetate=20:1 as eluent afford 1.55 g (85%) M as a yellow solid; Rf 0.26 (Hexane/EtOAC 15:1); 1H NMR (DMSO-d6) δ 2.48 (s, 3 H), 2.63 (s, 3 H), 6.77 (s, 1 H).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customthe solvent was removed under reduced pressure
  3. customto afford a dark residue
  4. customThe solvent was evaporated
  5. customto afford a plug

Sources & evidence

ORD record
ord-9412d787c3bf4a188e9a06863f64dc80
Source dataset
uspto-grants-2015_09
Patent number
US09139590B2

Reaction notes

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