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

HRID 2252410ノート

反応式

HRID 2252410 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-112b4fdd942e49e1970f62537c561cf9
出典データセット
uspto-grants-2008_01
特許番号
US07321033B2

反応ノート

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