Isopropanol → 9-(2-furanylmethyl)-N-(4-piperidinyl)-9H-purin-8-amine hemihydrate

HRID 2248808Notes

Reaction equation

HRID 2248808 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]([NH:16][CH:17]2[CH2:22][CH2:21][N:20](C(OCC)=O)[CH2:19][CH2:18]2)=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][CH:12]=2.[OH-].[K+].CC(O)C>O>[OH2:1].[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]([NH:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][CH:12]=2.[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]([NH:16][CH:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][CH:12]=2

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 19785341ethyl 4-[[9-(2-furanylmethyl)-9H-purin-8-yl]amino]-1-piperidinecarboxylate

Product 1

HCID 678787309-(2-furanylmethyl)-N-(4-piperidinyl)-9H-purin-8-amine hemihydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 60.5 parts of ethyl 4-[[9-(2-furanylmethyl)-9H-purin-8-yl]amino]-1-piperidinecarboxylate, 90 parts of potassium hydroxide, 800 parts of 2-propanol and 20 parts of water was stirred for 48 hours at reflux temperature. The reaction mixture was evaporated. The reaction mixture was poured into water while stirring. The product was filtered off and dried, yielding a first fraction of 36.2 parts of 9-(2-furanylmethyl)-N-(4-piperidinyl)-9H-purin-8-amine hemihydrate. The aqueous phase was extracted with dichloromethane. The organic layer was dried, filtered and evaporated. The oily residue was stirred in acetonitrile and 2,2'-oxybispropane. The product was filtered off and dried, yielding a second fraction of 5.6 parts of 9-(2-furanylmethyl)-N-(4-piperidinyl)-9H-purin-8-amine. Total yield 41.8 parts (86%) of 9-(2-furanylmethyl)-N-(4-piperidinyl)-9H-purin-8-amine hemihydrate; mp. 164.1° C. (compound 33).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionThe reaction mixture was poured into water
  4. stirringwhile stirring
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-8276feb143e44e58b3cb35a5036337de
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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