Tetrahydrofurfuryl alcohol → HCID 57699607, compound

HRID 1011029Notes

Reaction equation

HRID 1011029 reaction equation
[CH2:1]([OH:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.CC(C)([O-])C.[Na+].Cl[C:15]1[N:23]=[C:22]2[C:18]([N:19]=[CH:20][N:21]2[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[C:17]([NH2:30])[N:16]=1>COCCOC>[O:6]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:1][O:7][C:15]1[N:23]=[C:22]2[C:18]([N:19]=[CH:20][N:21]2[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[C:17]([NH2:30])[N:16]=1

Participants

5

Reactant 3

HCID 7360Tetrahydrofurfuryl alcoholHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineHCID 23676156Sodium t-butoxide

Product 1

HCID 57699607HCID 57699607, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

Tetrahydrofurfuryl alcohol (4.09 g) was diluted with 1,2-dimethoxyethane (20 mL). To this solution was added sodium tert-butoxide (3.84 g) gradually. The resultant reaction mixture was stirred until homogeneous (orange solution) before 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (2.53 g) was added. The reaction mixture was then heated to 110° C. (external) overnight under nitrogen. The reaction mixture was quenched with water (100 mL) and extracted with ethyl acetate (100 mL, 3 times). The organic layer was separated, combined and then dried by passing through a hydrophobic frit. This was evaporated under reduced pressure and the resultant material was then purified by silica chromatography eluting with 0-100% ethyl acetate: cyclohexane followed by methanol. An ISCO pump fault was detected whilst eluting with methanol, this line carried ethyl acetate previously and it was not known if the fault existed when eluting with ethyl acetate: cyclohexane. The appropriate fractions were evaporated to give the title compound as a solid (1.7258 g). This material was used in the next stage without further purification.

Workup

  1. customThe resultant reaction mixture
  2. additionwas added
  3. customThe reaction mixture was quenched with water (100 mL)
  4. extractionextracted with ethyl acetate (100 mL, 3 times)
  5. customThe organic layer was separated
  6. customdried
  7. customThis was evaporated under reduced pressure
  8. customthe resultant material was then purified by silica chromatography
  9. washeluting with 0-100% ethyl acetate
  10. washwhilst eluting with methanol
  11. washeluting with ethyl acetate
  12. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-a6173266a04846e7a4052a8af2d74595
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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