Phosphorus oxychloride → 4-Chloro-6-(2-furanyl)-2-pyrimidinamine

HRID 583813Notes

Reaction equation

HRID 583813 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1.O=P(Cl)(Cl)[Cl:16]>>[NH2:1][C:2]1[N:7]=[C:6]([Cl:16])[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178508968HCID 178508968, compound

Product 1

HCID 223243064-Chloro-6-(2-furanyl)-2-pyrimidinamine

Procedure

A solution of 2-amino-4-hydroxy-6-(2-furyl)pyrimidine (1.40 g, 7.9 mmol) in POCl3 (4 mL) was refluxed under argon for 2 h. The POCl3 was distilled; the residue was diluted with EtOAc and poured over iced saturated NaHCO3. The layers were separated and the aqueous was extracted with EtOAc (100 mL). The combined extracts was washed with saturated NaCl, dried (MgSO4), and the solvent removed at reduced pressure to afford 0.5 g of crude product, which was used without further purification. TLC (20% EtOAc/80% hexane) Rf 0.26; 1H-NMR (DMSO-d6) δ 6.68 (dd, J=1.7, 3.4 Hz, 1H), 6.94 (s, 1H), 7.25 (dd, J=1, 3.7 Hz, 1H), 7.91 (dd, J=0.8, 1.9 Hz, 1H).

Workup

  1. distillationThe POCl3 was distilled
  2. additionthe residue was diluted with EtOAc
  3. additionpoured over iced saturated NaHCO3
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with EtOAc (100 mL)
  6. washThe combined extracts was washed with saturated NaCl
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-cf611ab3098548c68a4b63b88e9c7030
Source dataset
uspto-grants-2005_08
Patent number
US06924290B2

Reaction notes

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