2-chloro-N-(phenylmethyl)-9-(tetrahydro-3-thienyl)-9H-purin-6-amine → N2-(4-amino-cyclohexyl)-N6-(phenylmethyl)-9-(tetrahydro-3-thienyl)-9H-purine-2,6-diamine Dihydrochloride

HRID 1244893Notes

Reaction equation

HRID 1244893 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH:19]2[CH2:23][CH2:22][S:21][CH2:20]2)=[C:12]([NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:11]=1>O>[ClH:9].[ClH:9].[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH:19]3[CH2:23][CH2:22][S:21][CH2:20]3)=[C:12]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:11]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 219229482-chloro-N-(phenylmethyl)-9-(tetrahydro-3-thienyl)-9H-purin-6-amineHCID 178511674HCID 178511674, compound

Product 1

HCID 18457593N2-(4-amino-cyclohexyl)-N6-(phenylmethyl)-9-(tetrahydro-3-thienyl)-9H-purine-2,6-diamine DihydrochlorideYield 131.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

400 mg of trans-1,4-diaminocyclohexane is taken to a temperature of 60 to 70° C., then 119 mg of the product obtained in Stage 2 above is added and the reaction medium is taken to a temperature of 130 to 140° C. for 3 hours, then left to return to ambient temperature, 5 ml of water is added followed by extracting with 3×10 ml of ethyl acetate, washing with 10 ml of water and 5 ml of an aqueous solution of sodium chloride, drying and evaporating to dryness. After purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2, followed by salification with 1.4N hydrochloric acid in ethanol, leaving to crystallize for 2 days at ambient temperature, separating, washing with 10 ml of ethanol and drying at a temperature of approximately 50° C. In this way 112 mg of expected product is obtained in the form of crystals white/cream.

Workup

  1. customis taken to a temperature of 60 to 70° C.
  2. waitleft
  3. customto return to ambient temperature
  4. extractionby extracting with 3×10 ml of ethyl acetate
  5. washwashing with 10 ml of water and 5 ml of an aqueous solution of sodium chloride
  6. customdrying
  7. customevaporating to dryness
  8. customAfter purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2
  9. customleaving
  10. customto crystallize for 2 days at ambient temperature
  11. customseparating
  12. washwashing with 10 ml of ethanol
  13. customdrying at a temperature of approximately 50° C

Sources & evidence

ORD record
ord-537e9612c64d4f339a9a548a12cd3deb
Source dataset
uspto-grants-2006_10
Patent number
US07122669B1

Reaction notes

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