Cyclohexanol → 9-Cyclohexyl-8-(1-methyl-4-phenyl-1H-imidazol-5-yl)-9H-purin-6-amine

HRID 32546Notes

Reaction equation

HRID 32546 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][N:16]1[C:20]([C:21]2[NH:22][C:23]3[C:28]([N:29]=2)=[C:27]([NH2:30])[N:26]=[CH:25][N:24]=3)=[C:19]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:18]=[CH:17]1.[CH:37]1(O)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH:37]1([N:22]2[C:21]([C:20]3[N:16]([CH3:15])[CH:17]=[N:18][C:19]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[N:29][C:28]3[C:23]2=[N:24][CH:25]=[N:26][C:27]=3[NH2:30])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 178481246HCID 178481246, compound

Product 1

HCID 103619899-Cyclohexyl-8-(1-methyl-4-phenyl-1H-imidazol-5-yl)-9H-purin-6-amineYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.1 mL) was added to a solution of 8-(1-methyl-4-phenyl-1H-imidazol-5-yl)-9H-purin-6-amine (Example 3) (75 mg), cyclohexanol (0.07 mL) and triphenylphosphine (0.14 g) in THF (4 mL) under an inert atmosphere. After stirring at ambient temperature for 48 hours the reaction mixture was heated at 40° C. for 48 hours and then at 55° C. for 24 hours. The solvent was then evaporated in vacuo to give a brown oil. Purification by preparative LCMS gave the title compound as a white solid (11 mg, 11%);

Workup

  1. temperaturewas heated at 40° C. for 48 hours
  2. waitat 55° C. for 24 hours
  3. customThe solvent was then evaporated in vacuo
  4. customto give a brown oil
  5. customPurification by preparative LCMS

Sources & evidence

ORD record
ord-d48c83fc7ad5411db027175bd48b26b8
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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