Cyclohexanemethanol → HCID 5329578, compound

HRID 380446Notes

Reaction equation

HRID 380446 reaction equation
[Na].[CH:2]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl[C:11]1[N:19]=[CH:18][N:17]=[C:16]2[C:12]=1[NH:13][CH:14]=[N:15]2>C(O)(=O)C>[CH:2]1([CH2:8][O:9][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[NH:13][CH:14]=[N:15]3)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7507CyclohexanemethanolHCID 53592776-ChloropurineHCID 5360545Sodium2×

Product 1

HCID 5329578HCID 5329578, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Sodium (0.4 g, 17.4 mmol) was added to stirred cyclohexylmethanol (10 ml) under nitrogen. The reaction was stirred at 100° C. until no sodium remained. 6-Chloropurine (500 mg, 3.24 mmol) was added, and the reaction was stirred under nitrogen at 100° C. for 5 days. After cooling to room temperature, the mixture was neutralised with glacal acetic acid and the solvent was removed in vacuo. Water (20 ml) was added and the product was extracted into dichloromethane (3×30 ml). The combined organic extracts were dried over MgSO4, and the volume of the solvent was doubled. After filtering hot and removal of the solvent, recrystallisation from ethyl acetate gave the title compound as a white crystalline solid (600 mg, 70%), m.p. 210-211° C.; (Found: C, 62.30; H, 6.93; N, 24.36. Calc. for C12H16N4O: C, 62.05; H, 6.94; N, 24.12%); νmax (cm−1) 3108, 3050,2930, 2849, 2801 (NH, C—H); δH (200 MHz, d6-DMSO) 8.479 (1H, s, C(2)H or C(8)H), 8.388 (1H, s, C(2)H or C(8)H), 4.348 (2H, d, J=6.2 Hz, OCH2), 1.854-1.692 (6H, m, cyclohexyl), 1.357-0.984 (5H, m, cyclohexyl); δC (50 MHz, d6-DMSO) 159.40, 155, 151.57, 142.88, 118, 71.41 (OCH2), 37.08, 29.40, 26.24, 25.47 (cyclohexyl); m/z 233 (MH+, 76%), 202 (33), 149 ([M—C6H11]+, 32%), 137 (100), 120 ([MH—C7H13O]+, 44%), 108 (30), 93 (27), 81 (65), 67 (62), 55 (88), 41 (89).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed in vacuo
  3. additionWater (20 ml) was added
  4. extractionthe product was extracted into dichloromethane (3×30 ml)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationAfter filtering hot
  7. customremoval of the solvent, recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-6962026db8474c2780eceed4d82b9e9a
Source dataset
uspto-grants-2001_10
Patent number
US06303618B1

Reaction notes

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