Sodium Methoxide → HCID 178450376, compound

HRID 2197481Notes

Reaction equation

HRID 2197481 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH2:23][P:24]([CH3:29])(=[O:28])[O:25][CH2:26]C)[CH:20]=[CH:21][CH:22]=1.C[O-:32].[Na+]>CO>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:32])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH2:23][P:24]([CH3:29])(=[O:28])[O:25][CH3:26])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57816822ethyl (3-((6-amino-8-bromo-2-butoxy-9H-purin-9-yl)methyl)phenyl)methyl(methyl)phosphinate

Product 1

HCID 178450376HCID 178450376, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 69 (130.4, 0.26 mmol) in methanol (10 mL) was slowly added sodium methoxide (283.8 mg, 5.25 mmol). The mixture was heated to 70° C. for 3 hours at which time Dowex resin was added to quench any remaining methoxide. The resin was filtered off and the solvent evaporated. The product was stirred in 6N HCl over night (16 hr) after which time the solvent was evaporated to give 70 as a white solid, the crude product was carried through to the next step. LCMS: m/z for C20H28N5O4P++H observed 420.2 at 1.92 minutes of a 3.5 minute run, eluting 5-95% CH3CN in H2O.

Workup

  1. additionwas added
  2. customto quench any remaining methoxide
  3. filtrationThe resin was filtered off
  4. customthe solvent evaporated
  5. customwas evaporated

Sources & evidence

ORD record
ord-97ef7488b8e94c3abaa6a19f42dfa89d
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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