Phosphorus oxychloride → HCID 86626009, compound

HRID 2420987Notes

Reaction equation

HRID 2420987 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH:6]1([C:9]2[O:13][C:12]([C:14]3[C:15](O)=[N:16][C:17]([S:20][CH3:21])=[N:18][CH:19]=3)=[N:11][N:10]=2)[CH2:8][CH2:7]1.C(=O)([O-])O.[Na+]>>[Cl:3][C:15]1[C:14]([C:12]2[O:13][C:9]([CH:6]3[CH2:8][CH2:7]3)=[N:10][N:11]=2)=[CH:19][N:18]=[C:17]([S:20][CH3:21])[N:16]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178503411HCID 178503411, compound

Product 1

HCID 86626009HCID 86626009, compoundYield 79%

Conditions

Temperature
60 °C

Procedure

Phosphorus oxychloride (15 mL) was added to 5-(5-cyclopropyl[1,3,4]oxadiazol-2-yl)-4-hydroxy-2-methylthiopyrimidine (6.26 g) obtained in Step 6, and the mixture was stirred at 60° C. for 30 minutes. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was added to a saturated aqueous sodium hydrogencarbonate solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. Diethyl ether was added to the residue to precipitate crystals. The resulting crystals were collected by filtration and dried thoroughly under reduced pressure to give 4-chloro-5-(5-cyclopropyl[1,3,4]oxadiazol-2-yl)-2-methylthiopyrimidine (5.31 g, yield 79%).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionDiethyl ether was added to the residue
  6. customto precipitate crystals
  7. filtrationThe resulting crystals were collected by filtration
  8. customdried thoroughly under reduced pressure

Sources & evidence

ORD record
ord-f988cccaac2e4d82b3873ecc0d5ddb1d
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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