Guanidine Hydrochloride → 5-Amino-3H-thiazolo[4,5]pyrimidine-2-one

HRID 2252410Notes

Reaction equation

HRID 2252410 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:9])[S:5][C:6]=1[CH:7]=O.Cl.[NH2:11][C:12]([NH2:14])=[NH:13].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:14][C:12]1[N:11]=[CH:7][C:6]2[S:5][C:4](=[O:9])[NH:3][C:2]=2[N:13]=1

Participants

6

Reactant 4

HCID 5742Guanidine HydrochlorideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 121980294-Chloro-2-oxo-2,3-dihydro-1,3-thiazole-5-carbaldehyde

Product 1

HCID 247640395-Amino-3H-thiazolo[4,5]pyrimidine-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Compound 85 (1.22 g, 7.47 mmol), guanidine hydrochloride (2.13 g, 22.4 mmol), K2CO3 (1.03 g, 7.47 mmol), and NaHCO3 (1.88 g, 22.3 mmol) was suspended in DMF and heated for two days at 110° C. Upon consumption of the starting material as determined by TLC, the solvent was removed under vacuurn. The solid residue was triturated with water. An analytically pure sample of 86 was obtained by HPLC (ODS-A C18; 3-97% CH3CN/H2O gradient; 1.0 mL/min). Tan solid: HPLC Rt=1.63 min; Rf=0.45 (2% H2O, 8% Methanol, 90% Ethyl acetate); 1H NMR (400 MHz, d6-DMSO) δ 8.11 (s, 1H), 6.67 (s, 2H); MS (+)-ES [M+H]+ 169; Elemental analysis for C5H4N4OS.0.1 CH3CN.0.1 H2O: calc'd: C, 35.88; H, 2.61; N, 32.99; S, 18.42. Found: C, 35.96; H, 2.75; N, 32.56; S, 18.42.

Workup

  1. customUpon consumption of the starting material
  2. customthe solvent was removed under vacuurn
  3. customThe solid residue was triturated with water

Sources & evidence

ORD record
ord-112b4fdd942e49e1970f62537c561cf9
Source dataset
uspto-grants-2008_01
Patent number
US07321033B2

Reaction notes

Loading…