Methanol → HCID 10140332, compound

HRID 324373Notes

Reaction equation

HRID 324373 reaction equation
[Na].[CH2:2]([N:4]([CH2:26][CH2:27][CH2:28][CH3:29])[C:5]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[N:12]([C:17]3[C:22]([Cl:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=3[Cl:25])[N:13]=[C:14]([S:15][CH3:16])[C:6]=12)[CH3:3].[CH3:30][OH:31]>>[CH2:2]([N:4]([CH2:26][CH2:27][CH2:28][CH3:29])[C:5]1[N:10]=[C:9]([O:31][CH3:30])[N:8]=[C:7]2[N:12]([C:17]3[C:22]([Cl:23])=[CH:21][C:20]([Cl:24])=[CH:19][C:18]=3[Cl:25])[N:13]=[C:14]([S:15][CH3:16])[C:6]=12)[CH3:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545Sodium2×HCID 10184234HCID 10184234, compound

Product 1

HCID 10140332HCID 10140332, compound

Procedure

To 1 ml of methanol was added sodium (25 mg) and the mixture was stirred until all the sodium was dissolved completely. The resulting solution was treated with ethyl-butyl-[6-chloro-3-methylsulfanyl-1-(2,4,6trichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4-yl]amine (100 mg, 0.21 mmol) and heated at reflux for 3 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give an oil residue. The oil residue was purified by silica gel column chromatography to give 73 mg of the title compound as a colorless oil. 1H NMR (CDCl3):0.96(t,3H), 1.35(t,3H), 1.42(m,2H), 1.71(m,2H), 2.63(s,3H), 3.74(dd,2H), 3.86(q,2H), 3.91(s,3H), 7.46(s,2H)ppm.

Workup

  1. dissolutionwas dissolved completely
  2. temperatureheated
  3. temperatureat reflux for 3 hours
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customto give an oil residue
  9. customThe oil residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6fc87bbef68b4ac29579a5a5c2b20c8d
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Reaction notes

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