2-Methylpyridine → HCID 492870, compound

HRID 1637780Notes

Reaction equation

HRID 1637780 reaction equation
O[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[N:5]=[C:4]([CH:20]=[N:21]O)[CH:3]=1.O=P(Cl)(Cl)[Cl:25].N1C=CC=CC=1C>>[Cl:25][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)[N:5]=[C:4]([C:20]#[N:21])[CH:3]=1

Participants

4

Reactant 3

HCID 79752-MethylpyridineHCID 24813Phosphorus oxychlorideHCID 178526346HCID 178526346, compound

Product 1

HCID 492870HCID 492870, compound

Procedure

6-hydroxy-2-(2-naphthylmethyl)thio-4-pyrimidine carboxaldehyde oxime (720 mg, 2.31 mmol), POCl3 (3 ml), and 2-picoline (0.5 ml) are heated to reflux for 2 hrs. The reaction mixture is poured onto ice/water, extracted thrice with ethyl acetate, dried with MgSO4, and concentrated in vacuo. The product is purified by chromatography (SiO2, ethyl acetate/hexane, 5/95): 524 mg (1.67 mmol, 73%), mp 120-121° C.

Workup

  1. temperatureto reflux for 2 hrs
  2. additionThe reaction mixture is poured onto ice/water
  3. extractionextracted thrice with ethyl acetate
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product is purified by chromatography (SiO2, ethyl acetate/hexane, 5/95)

Sources & evidence

ORD record
ord-8173948c91d74f37a749d575ddc7db1e
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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