Sodium Methoxide → HCID 57699814, compound

HRID 1011019Notes

Reaction equation

HRID 1011019 reaction equation
Br[C:2]1[N:3]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[N:5]=2.[CH3:26][O-:27].[Na+]>CO>[CH:14]1([CH2:13][O:12][C:6]2[N:5]=[C:4]3[C:9]([N:10]=[C:2]([O:27][CH3:26])[N:3]3[CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)=[C:8]([NH2:11])[N:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57699806HCID 57699806, compound

Product 1

HCID 57699814HCID 57699814, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

8-Bromo-2-[(cyclohexylmethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (0.8151 g) was refluxed with 30% (w/v) sodium methoxide in methanol (1.1 mL) diluted with anhydrous methanol (6.0 mL). The suspension was refluxed (70° C. external) overnight. The reaction was partitioned between ethyl acetate (50 mL) and saturated aqueous ammonium chloride solution (50 mL). The organic layer was separated and the aqueous layer was re-extracted with ethyl acetate (50 mL). The organic layers were combined and washed with brine (50 mL) and separated before then being dried by passing through a hydrophobic frit. Evaporation under reduced pressure gave crude title compound as foam (0.7132 g) used without purification.

Workup

  1. customThe reaction was partitioned between ethyl acetate (50 mL) and saturated aqueous ammonium chloride solution (50 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was re-extracted with ethyl acetate (50 mL)
  4. washwashed with brine (50 mL)
  5. customseparated
  6. custombefore then being dried
  7. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-bc98a8bc242f46aa9d38ff6da914e9d8
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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