Potassium Carbonate → HCID 21846383, compound

HRID 617793Notes

Reaction equation

HRID 617793 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:4](O)[N:3]=1.[Cl:19]S(O)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>P(Cl)(Cl)(Cl)=O>[ClH:19].[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:4]([Cl:19])[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24638Chlorosulfonic acidHCID 178508961HCID 178508961, compound

Product 1

HCID 21846383HCID 21846383, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
95 °C

Procedure

2-Amino-6-hydroxy-4-(naphth-1-yl)-pyrimidine (900 mg) was added to a solution of chlorosulfonic acid (0.05 mL) in 2.5 mL of phosphorus oxychloride, and the mixture was stirred at 95° C. for 6 hours. The mixture was poured onto ice, neutralized with potassium carbonate, and extracted with ethyl acetate. The crude product (70 mg) was purified by silica gel chromatography, eluting with methylene chloride, and treated with hydrochloric acid-ethanol to give 2-amino-6-chloro-4-(naphth-1-yl)-pyrimidine hydrochloride (25 mg), m.p. 248-250° C.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. customThe crude product (70 mg) was purified by silica gel chromatography
  4. washeluting with methylene chloride
  5. additiontreated with hydrochloric acid-ethanol

Sources & evidence

ORD record
ord-b979d4caeb9b42b48298a26496f40625
Source dataset
uspto-grants-1999_09
Patent number
US05952331

Reaction notes

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