Methanol → 2-Butoxy-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 558449Notes

Reaction equation

HRID 558449 reaction equation
[Na].Br[C:3]1[N:4]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:5]2[C:10]([N:11]=1)=[C:9]([NH2:12])[N:8]=[C:7]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])[N:6]=2.[CH3:24][OH:25]>>[CH2:14]([O:13][C:7]1[N:6]=[C:5]2[C:10]([N:11]=[C:3]([O:25][CH3:24])[N:4]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[C:9]([NH2:12])[N:8]=1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 231585488-Bromo-2-butoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 231585192-Butoxy-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Conditions

Temperature
65 °C

Procedure

Sodium (3.7 g) was added to absolute methanol (400 ml) under a nitrogen atmosphere. To this solution was added the product (28.5 g) from step (iii) and the mixture was stirred at 65° C. for 9 h. The mixture was concentrated in vacuo and 500 ml of water added. The aqueous phase was extracted with EtOAc and washed with brine and dried. The subtitle compound was obtained after crystallisation from diethyl ether. Yield 14.2 g.

Workup

  1. concentrationThe mixture was concentrated in vacuo and 500 ml of water
  2. additionadded
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washwashed with brine
  5. customdried

Sources & evidence

ORD record
ord-7635e8dc8dd24d21b633c3fcd8804545
Source dataset
uspto-grants-2011_11
Patent number
US08063051B2

Reaction notes

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