Sodium Methoxide → HCID 21874528, compound

HRID 732998Notes

Reaction equation

HRID 732998 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:28]2[O:29][CH:30]=[CH:31][CH:32]=2)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:20]=[C:19]4[C:15]([CH:16]=[CH:17][N:18]4C(OC(C)(C)C)=O)=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.C[O-].[Na+]>CO>[O:29]1[CH:30]=[CH:31][CH:32]=[C:28]1[C:4]1[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:20]=[C:19]4[C:15]([CH:16]=[CH:17][NH:18]4)=[CH:14][CH:13]=3)[C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 21874612HCID 21874612, compound

Product 1

HCID 21874528HCID 21874528, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 6-(5-amino-7-(2-furyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine-3-ylmethyl)indole-1-carboxylate (135 mg, 4.08 mmol), and NaOMe (22 mg, 4.08 mmol) in MeOH (10 mL) was refluxed for 1 h, treated with NaOMe (110 mg, 20.4 mmol), refluxed for a further 4 h then stirred at room temperature for 17 h. The mixture was concentrated in vacuo to half volume and the resulting precipitate was filtered and washed with H2O to give the title compound (90 mg, 96%) as a cream solid.

Workup

  1. temperaturewas refluxed for 1 h
  2. temperaturerefluxed for a further 4 h
  3. concentrationThe mixture was concentrated in vacuo to half volume
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with H2O

Sources & evidence

ORD record
ord-0aff96a8f3f34b23a4c5c9145c793ccd
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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