2-Methoxyethanol → [2-(Methoxy)ethyl]oxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011023Notes

Reaction equation

HRID 1011023 reaction equation
CC(C)([O-])C.[K+].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.[CH3:24][O:25][CH2:26][CH2:27][OH:28]>>[CH3:24][O:25][CH2:26][CH2:27][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

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 127778192-Chloro-9-(tetrahydropyran-2-yl)adenineHCID 23665647Potassium tert-butoxide

Product 1

HCID 57699621[2-(Methoxy)ethyl]oxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Conditions

Temperature
85 °C

Procedure

Potassium tert.-butoxide (46.5 g, 475 mmol) was added to 2-methoxyethanol (200 mL) in 20 min at room temperature, then 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (30 g) was added and the resulted mixture was heated at 80-90° C. for about 3 h. Evaporation of most of the solvent, to the residue was added 100 ml of water, stirred for 1 h at 0° C., filtered and dried. This gave product (30 g, 87%) that was almost identical to that from Intermediate 119, method A.

Workup

  1. customEvaporation of most of the solvent
  2. additionto the residue was added 100 ml of water
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-1f566357d44b48dda9bc9aad18dcf980
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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