Isobutanol → 2-[(2-Methylpropyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

HRID 1011014Notes

Reaction equation

HRID 1011014 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([NH2:18])[N:3]=1.CC(C)([O-])C.[Na+].[CH3:25][CH:26]([CH3:29])[CH2:27][OH:28]>>[CH3:25][CH:26]([CH3:29])[CH2:27][O:28][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([NH2:18])[N:3]=1

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 23676156Sodium t-butoxideHCID 576998042-Chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

Product 1

HCID 576997722-[(2-Methylpropyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

Conditions

Temperature
105 °C

Procedure

2-Chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (0.20 g) was added to a suspension of 2-methyl-1-propanol (2 mL) and sodium tert-butoxide (0.288 g). The mixture was heated in a microwave for 30 minutes at 105° C. The reaction mixture was washed with water after diluting with ethyl acetate (50 mL). The organic was separated and dried by passing through a hydrophobic frit before volatiles were stripped off under reduced pressure to give a pinkish solid. This material was triturated with diethyl ether and filtered to give the title compound as a pinkish solid (91.1 mg).

Workup

  1. washThe reaction mixture was washed with water
  2. additionafter diluting with ethyl acetate (50 mL)
  3. customThe organic was separated
  4. customdried
  5. customto give a pinkish solid
  6. customThis material was triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-960dc7b4572c4b668f9ce12fdbec0f1f
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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