Water → 2-[(2-Cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011055Notes

Reaction equation

HRID 1011055 reaction equation
CC(C)([O-])C.[Na+].[CH:7]1([CH2:10][CH2:11][OH:12])[CH2:9][CH2:8]1.Cl[C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[C:16]([NH2:29])[N:15]=1.O>COCCOC>[CH:7]1([CH2:10][CH2:11][O:12][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[CH:19][N:20]3[CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][O:24]3)=[C:16]([NH2:29])[N:15]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 1376422-Cyclopropylethan-1-olHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineHCID 23676156Sodium t-butoxide

Product 1

HCID 576996002-[(2-Cyclopropylethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a stirring solution of sodium tert.-butoxide (13.45 g) in DME (80 ml) was added dropwise under nitrogen a solution of 2-cyclopropylethanol (12.1 g) in DME (40 ml) over 5 min. After 30 min 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (11.84 g) was added and the stirring mixture refluxed for 20 h. After cooling the mixture was treated with water and extracted twice with ethyl acetate. The combined extracts were washed with water then brine, dried by passing through a hydrophobic frit and evaporated to a brown oil. This was re-evaporated twice from toluene then purified on a silica column using an ISCO Companion, eluting with methanol:ethyl acetate (0-12%) to give the title compound. Yield 6.53 gm.

Workup

  1. temperaturethe stirring mixture refluxed for 20 h
  2. temperatureAfter cooling the mixture
  3. extractionextracted twice with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialbrine, dried
  6. customevaporated to a brown oil
  7. customThis was re-evaporated twice from toluene
  8. customthen purified on a silica column
  9. washeluting with methanol

Sources & evidence

ORD record
ord-8224413198ae4cf08373bcf6f291ecc1
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…