Sodium Methoxide → HCID 12971791, compound

HRID 2227789Notes

Reaction equation

HRID 2227789 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[CH2:20][CH2:21][CH2:22][CH3:23])=[C:13](Cl)[N:12]=2)=[CH:6][N:5]=1)[CH3:2].[CH2:25]([O:27]C1C=CC(NC2N=C3C(N(CCCC)C=N3)=C(Cl)N=2)=CN=1)C.C[O-].[Na+]>CO>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:19]=[C:18]3[C:14]([N:15]=[CH:16][N:17]3[CH2:20][CH2:21][CH2:22][CH3:23])=[C:13]([O:27][CH3:25])[N:12]=2)=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 12971790HCID 12971790, compoundHCID 18474724HCID 18474724, compound

Product 1

HCID 12971791HCID 12971791, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of a 4:1 mixture of 2-[(2-Ethoxypyrid-5-yl)amino]-6-chloro-9-butyl-9H-purine and 2-[(2-Ethoxypyrid-5-yl)amino]-6-chloro-7-butyl-7H-purine (214 mg; 0.62 mmol) in methanol (15 mL) is treated with sodium methoxide (4 mL of a 25% wt. solution in methanol) and the mixture is stirred at room temperature for three days. The reaction mixture is concentrated in vacuo , the residue is treated with water (30 mL), neutralized with acetic acid, and extracted with ethyl acetate (3×40 mL). The combined organic extracts are washed with water (2×30 mL) and brine (1×30 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo . The residue is purified by preparative thin layer chromatography on silica gel by elution with ethyl acetate-hexane (3:1) to afford 2-[(2-Ethoxypyrid-5-yl)amino]-6-methoxy-9-butyl-9H-purine (94 mg), m.p. 174-176° C. (compound 1).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionthe residue is treated with water (30 mL)
  3. extractionextracted with ethyl acetate (3×40 mL)
  4. washThe combined organic extracts are washed with water (2×30 mL) and brine (1×30 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by preparative thin layer chromatography on silica gel by elution with ethyl acetate-hexane (3:1)

Sources & evidence

ORD record
ord-55ee1c38cc404decb3dc660dd27bccea
Source dataset
uspto-grants-2002_07
Patent number
US06414147B1

Reaction notes

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