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

HRID 2252410노트

반응식

HRID 2252410 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-112b4fdd942e49e1970f62537c561cf9
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07321033B2

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