Hydrochloric Acid → HCID 135508876, compound

HRID 1757405Notes

Reaction equation

HRID 1757405 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][CH:13]3[CH2:17][O:16]C(C)(C)[O:14]3)[C:6]=2[N:7]=1.Cl>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[S:10][C:9](=[O:11])[N:8]([CH2:12][CH:13]([OH:14])[CH2:17][OH:16])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136062699HCID 136062699, compound

Product 1

HCID 135508876HCID 135508876, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-amino-3-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione(200 mg, 0.67 mmol) and a solution of hydrogen chloride in MeOH (10%, 20 mL) was protected from moisture and stirred at ambient temperature for 45 min. The solution was evaporated and the residue was stirred with H2O (20 mL). The mixture was immediately made basic (pH=9) by the addition of cone. NH4OH and then acidified (pH=6) withAcOH. The mixture was allowed to stand for 2 h and then the solid was collected by filtration, washed with H2O (50 mL) and dried in vacuumat 95° C. for 16 h.; 100 mg (0.387 mmol, 57%), mp 248°-254° C. Ir (KBr): ν 3360 broad (OH, NH, NH2), and 1600 broad (C=O, C=C, C=N) cm-1. Uv, λ max (nm), (ε×10-3): pH 1, 302 (10.4), 250 (9.59), 222 (29.3); MeOH, 302 (9.16), 250 (8.71), 222 (26.9); pH 11, 292 (7.62), 250 (7.67), 224 1H nmr (DMSO-d6): δ3.68-3.73 (m, 2 H, CH2), 3.80-3.92 (m, 3 H, CH2 and OH), 4.63 (t, 1 H, CH), 4.87 (d, 1 H, OH), 6.90 (br s, 2 H, NH2) and (br s, 1 H, NH). Anal. Calc'dfor C8H10N4O4S (258.26): C, 37.21; H, 3.90; N, 21.69. Found: C, 36.81; H, 4.02; N, 21.26.

Workup

  1. customThe solution was evaporated
  2. stirringthe residue was stirred with H2O (20 mL)
  3. additionby the addition of cone
  4. waitto stand for 2 h
  5. filtrationthe solid was collected by filtration
  6. washwashed with H2O (50 mL)
  7. customdried in vacuumat 95° C. for 16 h.

Sources & evidence

ORD record
ord-7bbeb8e3deea4caab6e8bc2c30c9db1c
Source dataset
uspto-grants-1995_08
Patent number
US05446045

Reaction notes

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