HCID 135752745, compound → HCID 135508873, compound

HRID 1604241Notes

Reaction equation

HRID 1604241 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[S:10][C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][O:16]C(=O)C)[C:6]=2[N:7]=1>[NH4+].[OH-]>[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[S:10][C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[C:6]=2[N:7]=1

Participants

3

Reactant 1

HCID 135752745HCID 135752745, compound

Product 1

HCID 135508873HCID 135508873, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of 5-Amino-3-(4-acetoxybutyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (230 mg, 771 μmol) and conc. NH4OH (10 mL) was placed in a pressure bottle and stirred at ambient temperature for 18 h. The solution was evaporated under vacuum and the residual solid was stirred with H2O (10 mL). The solid was collected by filtration, crystallized from a MeOH:H2O mixture and dried in vacuum at 80° C. for 3 d; 120 mg (468 μmol, 61%), mp 258-260 ° C. Ir (KBr): ν3305 and 3189 (OH, NH, NH2), and 1650 broad (C=O, C=N) cm-1. Uv, λmax (nm), (ε×10-3): pH 1, 302 (9.83), 250 (8.47), 222 (30.3); H2O, 302 (9.70), 250 (8.37), 222 (30.4); pH 11, 292 (7.71), 250 (7.47), 224 (9.62). 1H nmr (DMSO-d6): δ1.35-1.42 (m, 2H, CH2), 1.60-1.68 (m, 2H, CH2), 3.38 (m, 2H, OCH2), 3.76 (t, 2H, NCH2), 4.40 (t, 1H, OH), 6.89 (br s, 2H, NH2), and 11.06 (br s, 1H, NH). Anal. Calc'd for C9H12N4O3S (256.28): C, 42.18; H, 4.72; N, 21.86. Found: 42.05; H, 4.67; N, 21.72.

Workup

  1. customThe solution was evaporated under vacuum
  2. stirringthe residual solid was stirred with H2O (10 mL)
  3. filtrationThe solid was collected by filtration
  4. customcrystallized from a MeOH
  5. dry with materialH2O mixture and dried in vacuum at 80° C. for 3 d

Sources & evidence

ORD record
ord-32c345f4ec694111917cf18b6bd022e1
Source dataset
uspto-grants-1999_11
Patent number
US05994321

Reaction notes

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