1-Butanol → HCID 20301001, compound

HRID 1044844Notes

Reaction equation

HRID 1044844 reaction equation
CC(C)([O-])C.[Na+].Cl[C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:10]([NH2:23])[N:9]=1.[CH2:24]([OH:28])[CH2:25][CH2:26][CH3:27]>>[CH2:24]([O:28][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:10]([NH2:23])[N:9]=1)[CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineHCID 23676156Sodium t-butoxide

Product 1

HCID 20301001HCID 20301001, compound

Conditions

Temperature
100 °C

Procedure

To butan-1-ol (76 mL) was added portion wise sodium tert-butoxide (15.2 g) (Note: reaction mixture gets warm). The above was stirred until homogeneous (˜15 min) before 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (10.0 g) was then added to the resultant pale yellow solution. The reaction mixture was then heated to 100° C., overnight. The reaction mixture was stripped to remove as much butan-1-ol as possible before being partitioned between diethyl ether and water. The diethyl ether phase was separated and the aqueous re-extracted further with diethyl ether. Combined organic layers dried over magnesium sulphate (anhydrous). Magnesium sulphate was filtered off and filtrate stripped to give brown viscous oil which was azeotroped with toluene (3 times) and placed under high vacuum overnight, transferred to new flask with dichloromethane and stripped, placed under high vacuum to give the title compound as a brown glass (9.45 g).

Workup

  1. additionwas then added to the resultant pale yellow solution
  2. customto remove as much butan-1-ol as possible
  3. custombefore being partitioned between diethyl ether and water
  4. customThe diethyl ether phase was separated
  5. extractionthe aqueous re-extracted further with diethyl ether
  6. dry with materialCombined organic layers dried over magnesium sulphate (anhydrous)
  7. filtrationMagnesium sulphate was filtered off
  8. customto give brown viscous oil which
  9. customwas azeotroped with toluene (3 times)
  10. customplaced under high vacuum overnight
  11. customtransferred to new flask with dichloromethane

Sources & evidence

ORD record
ord-b138b20938a949cf85431222a2a063f3
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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