Thionyl Chloride → HCID 18647811, compound

HRID 1534014Notes

Reaction equation

HRID 1534014 reaction equation
[C:1]1([N:7]2[C:11]3=[N:12][CH:13]=[N:14][C:15]([NH:16][C@@H:17]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:18]O)=[C:10]3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl>C(Cl)Cl>[C:1]1([N:7]2[C:11]3[N:12]=[CH:13][N:14]4[CH2:18][C@H:17]([CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:16]=[C:15]4[C:10]=3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18647814HCID 18647814, compound

Product 1

HCID 18647811HCID 18647811, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Next, 300 mg of the above product (S)-β-[(1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol was dissolved in 15 ml CH2Cl2 followed by addition of 0.44 ml SOCl2. The reaction was heated to reflux for 3.5 hours. The solvent was then removed under a stream of nitrogen. The white solid was recrystallized from about 30% isopropyl alcohol/hexane followed by a second recrystallization from about 5%MeOH/butanone to yield 45 mg of (S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-3H-imidazo[1,2-c]pyrazolo[4,3-e]-pyrimidine after drying under vacuum at 39° C. for 5 days (m.p. 255° C.).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3.5 hours
  3. customThe solvent was then removed under a stream of nitrogen
  4. customThe white solid was recrystallized from about 30% isopropyl alcohol/hexane
  5. customfollowed by a second recrystallization from about 5%MeOH/butanone

Sources & evidence

ORD record
ord-f66cec92cc7548bf86a3e7ae020be119
Source dataset
uspto-grants-1992_02
Patent number
US05086176

Reaction notes

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