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2-chloro-N-phenyl-9-(tetrahydro-3-thienyl)-9H-purin-6-amine → N2-(4-aminocyclo-hexyl)-N6-phenyl-9-(tetrahydro-3-thienyl)-9H-purin-2,6-diamine Dihydrochloride

HRID 1244913
Notes
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Reaction equation

HRID 1244913 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][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]=1>>[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][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:11]=2)[CH2:4][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 219229282-chloro-N-phenyl-9-(tetrahydro-3-thienyl)-9H-purin-6-amineHCID 178511674HCID 178511674, compound

Product 1

HCID 18457589N2-(4-aminocyclo-hexyl)-N6-phenyl-9-(tetrahydro-3-thienyl)-9H-purin-2,6-diamine DihydrochlorideYield 127.9%

Procedure

The operation is carried out as in Stage 3 of Example 5 starting from 536 mg of trans-1,4-diaminocyclohexane and 156 mg of the product obtained in Stage 1 above, the reaction medium is taken to a temperature of approximately 140 to 145° C. for approximately 4 hours 30 minutes then left to return to ambient temperature. After purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2 salification is carried out with 1.4 N hydrochloric acid in ethanol, followed by separating, washing and drying at a temperature of approximately 50° C. In this way 145 mg of expected product is obtained in the form of pink beige crystals.

Workup

  1. waitthen left
  2. customto return to ambient temperature
  3. customAfter purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2 salification
  4. customby separating
  5. washwashing
  6. customdrying at a temperature of approximately 50° C

Sources & evidence

ORD record
ord-2ed82099136b4f288565db76e544fda5
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122669B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes