2-Methylpyridine → HCID 10546355, compound

HRID 1637789Notes

Reaction equation

HRID 1637789 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10](O)[N:9]=[C:8]([S:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[N:7]=1)=[O:5])[CH3:2].N1C=CC=CC=1C.O=P(Cl)(Cl)[Cl:34]>>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([Cl:34])[N:9]=[C:8]([S:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 79752-MethylpyridineHCID 24813Phosphorus oxychlorideHCID 178469372HCID 178469372, compound

Product 1

HCID 10546355HCID 10546355, compoundYield 70%

Procedure

A solution of 6-hydroxy-2-(2-naphthylmethylthio)-pyrimidine-4-carboxylic acid ethyl ester (2.32 g, 6.81 mmol) and 2-picoline (0.7 ml) in POCl3 (7 ml) were stirred at rt for 3 hrs, then poured onto ice. The solid was collected by filtration then heated briefly with NH4OH for 15 min. The solid was collected and recrystallized from methanol to yield 1.72 g (70%) of 6-chloro-2-(2-naphthylmethylthio)-pyrimidine-4-carboxylic acid ethyl ester, mp 95-96° C.

Workup

  1. additionpoured onto ice
  2. filtrationThe solid was collected by filtration
  3. temperaturethen heated briefly with NH4OH for 15 min
  4. customThe solid was collected
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-41a8fa61f6134319b7d9aa3c514f3b57
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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