Sodium Methoxide → HCID 136058955, compound

HRID 1634919Notes

Reaction equation

HRID 1634919 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:45])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[O:18][C@@H:17]([CH2:19][O:20]C(=O)C4C=CC=CC=4)[C@:15](C(=O)C4C=CC=CC=4)([OH:16])[C@:13]3(C(=O)C3C=CC=CC=3)[OH:14])[C:6]=2[N:7]=1.C[O-].[Na+]>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:45])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[O:18][C@@H:17]([CH2:19][OH:20])[C@H:15]([OH:16])[C@@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 136352430HCID 136352430, compound

Product 1

HCID 136058955HCID 136058955, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-3-(2′,3′,5′-O-tribenzoyl-β-L-ribofuranosyl)thiazolo[4,5-d]pyrimidine-2,7(6H)-dione 33 (1.09 g, 1.717 mmol) was dissolved in methanol (25 mL) and sodium methoxide (5.4 M in methanol, 0.64 mL) added. The solution stood at room temperature for 64 h. Most methanol was evaporated and water (20 mL) and Amberite H-Form (1.0 g) added. The suspension was stirred gently for 20 min and the resin filtered by suction, washed with water (2×10 mL). The filtrate was concentrated and the crude product was purified by crystallization from methanol to give 368 mg of 5-Amino-3-β-L-ribofuranosylthiazolo[4,5d]pyrimidine-2,7(6H)-dione 34 as a colorless solid.

Workup

  1. customMost methanol was evaporated
  2. additionwater (20 mL) and Amberite H-Form (1.0 g) added
  3. filtrationthe resin filtered by suction
  4. washwashed with water (2×10 mL)
  5. concentrationThe filtrate was concentrated
  6. customthe crude product was purified by crystallization from methanol

Sources & evidence

ORD record
ord-4b6cc2fcbabe49d1a25af7013e2ee7d3
Source dataset
uspto-grants-2003_01
Patent number
US06509320B1

Reaction notes

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