Sodium Methoxide → HCID 135508875, compound

HRID 1604246Notes

Reaction equation

HRID 1604246 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:35])[C:5]2[S:10][C:9](=[O:11])[N:8]([CH2:12][O:13][CH:14]([CH2:25][O:26]C(=O)C3C=CC=CC=3)[CH2:15][O:16]C(=O)C3C=CC=CC=3)[C:6]=2[N:7]=1.C[O-].[Na+]>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:35])[C:5]2[S:10][C:9](=[O:11])[N:8]([CH2:12][O:13][CH:14]([CH2:15][OH:16])[CH2:25][OH:26])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 137231703HCID 137231703, compound

Product 1

HCID 135508875HCID 135508875, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-Amino-3-(1,3-dibenzoyloxy-2-propoxymethyl)thiazolo[4,5-d]pyrimidine-2,7(3H, 6H)-dione (0.4 g, 0.798 mmol), sodium methoxide (0.2 g) and MeOH (100 mL) was stirred at ambient temperature for 18 h. Amberlite IR-120(H+) (1 g, washed with H2O, then MeOH) was added and the mixture was stirred until neutral. The resin was removed by filtration and the MeOH solution was evaporated. The residue was extracted with Et2O (2×50 mL) and then crystallized from H2O . The crystalline product was dried in vacuum at 90° C. for 2 days; 0.115 g (0.399 mmol, 50%), mp 256-258° C. Ir (KBr): ν3370, 3210 and 3170 (NH, NH2, OH), and 1650 broad(C=O, C=N) cm-1. Uv, λmax (nm) (ε×10-3): pH 1, 302 (9.62), 248 (9.16), 216 (27.6); MeOH, 302 (9.08), 248 (8.43), 216 (25.0); pH 11, 292 (7.37), 246 (8.04). 1H nmr (DMSO-d6): δ3.28-3.34 (m, 2H, CH2), 3.41-3.46 (m, 2H, CH2), 3.66 (t, 1H, CH), 4.53 (t, 2H, 2 OH), 5.24 (s, 2H, NCH2), 6.91 (br s, 2H, NH2), and 11.13 (br s, 1H, NH). Anal. Calc'd for C9H12N4O5S (288.28): C, 37.50; H, 4.08; N, 19.43. Found: C, 37.43; H, 4.08; N, 19.23.

Workup

  1. washAmberlite IR-120(H+) (1 g, washed with H2O
  2. additionMeOH) was added
  3. stirringthe mixture was stirred until neutral
  4. customThe resin was removed by filtration
  5. customthe MeOH solution was evaporated
  6. extractionThe residue was extracted with Et2O (2×50 mL)
  7. customcrystallized from H2O
  8. customThe crystalline product was dried in vacuum at 90° C. for 2 days

Sources & evidence

ORD record
ord-1b8a922a788b4f29987828944adec392
Source dataset
uspto-grants-1999_11
Patent number
US05994321

Reaction notes

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