1-Propanol → HCID 15232049, compound

HRID 1728916Notes

Reaction equation

HRID 1728916 reaction equation
[Na].[CH3:2][C@H:3]([NH:11][C:12]1[N:17]=[C:16](Cl)[N:15]=[C:14]2[N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:21][C:13]=12)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:28]([OH:31])[CH2:29][CH3:30]>[Na+].[Cl-]>[CH3:2][C@H:3]([NH:11][C:12]1[N:17]=[C:16]([O:31][CH2:28][CH2:29][CH3:30])[N:15]=[C:14]2[N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:20]=[CH:21][C:13]=12)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10311-Propanol2×HCID 5360545SodiumHCID 53672786HCID 53672786, compound

Product 1

HCID 15232049HCID 15232049, compound

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

Next, 324 mg sodium was reacted with 10 ml of n-propanol. To this, 640 mg of (S)-N-(1-methyl-2-phenylethyl) -1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-amine in 5 ml of n-propanol was added with stirring and the reaction was heated to 90° C. for 2 hours. It was then cooled, diluted with 200 ml saturated NaCl, and extracted with 200 ml CHCl3. The organic layer was dried over MgSO4, filtered, and concentrated to yield an oil which was purified by radial chromatography (30-50% Et2O/hexane) to yield after recrystallization from 30% Et2O/hexane 382 mg of product (m.p. 134°-136° C.). Proton NMR indicated ether was still present. The compound was then oven dried under vacuum for 6 hours to yield 318 mg of (S)-N-(1-methyl-2-phenylethyl)-1-phenyl-6-propoxy-1H-pyrazolo[3,4-d]pyrimidin-4-amine (m.p. 134°-136° C.).

Workup

  1. temperatureIt was then cooled
  2. extractionextracted with 200 ml CHCl3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield an oil which
  7. customwas purified by radial chromatography (30-50% Et2O/hexane)
  8. customto yield
  9. customafter recrystallization from 30% Et2O/hexane 382 mg of product (m.p. 134°-136° C.)
  10. customoven dried under vacuum for 6 hours

Sources & evidence

ORD record
ord-a02dfc6b4b9a4109896c26f4f919e7e2
Source dataset
uspto-grants-1994_07
Patent number
US05329007

Reaction notes

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