Water → N-(6-chloro-2-methylpyrimidin-4-yl)thiazol-2-amine

HRID 1685292

반응식

HRID 1685292 반응식
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10]([CH3:15])[N:9]=1.CC([O-])(C)C.[K+].O>C1COCC1>[Cl:7][C:8]1[N:9]=[C:10]([CH3:15])[N:11]=[C:12]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 21552-AminothiazoleHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 59200477N-(6-chloro-2-methylpyrimidin-4-yl)thiazol-2-amine수율 51.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a cool (0° C.), stirring suspension of 2-aminothiazole (3.05 g, 0.0305 mol), 4,6-dichloro-2-methylpyrimidine (5.84 g, 0.0358 mol) in THF (50 mL) was added dropwise over 10 minutes via addition funnel a solution of t-BuOK (40 mL, 30% wt in THF, 0.1069 mol). The reaction was allowed to slowly warm to room temperature overnight. To the reaction was added water (40 mL) and the resulting clear solution was extracted with chloroform and then chloroform/methanol (4:1). The combined extracts were concentrated to near dryness to give a precipitate. The solid was collected by filtration to give the title material (3.559 g) as a solid. The filtrate was concentrated to dryness and the resulting solid was dissolved in boiling methanol and allowed to precipitate overnight aided with the addition of some water. The solid was collected by filtration, washed with water and air dried to give the title material (1.451 g) as a solid. The aqueous layer from the extraction was acidified with 10% HCl and a precipitate was formed. The solid was collected by filtration, washed with water to give the title material (1.559 g) as a solid. The solids were combined to give the title material (6.569 g, 95%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 2.53 (3H, s), 6.90 (1H, s), 7.21 (1H, d, J=3.5 Hz), 7.46 (1H, d, J=3.5 Hz), 11.87 (1H, s). LC/MS (M+H)+: 227, 229. HPLC ret. time (Condition E): 1.427 min.

후처리

  1. temperatureto slowly warm to room temperature overnight
  2. extractionthe resulting clear solution was extracted with chloroform
  3. concentrationThe combined extracts were concentrated
  4. customto give a precipitate
  5. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-ae7a13355a4240baa53f9d7444165ff6
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148400B2

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