Water → 5-Chloro-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine

HRID 2197417노트

반응식

HRID 2197417 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([NH:11]C(=O)OCC)=S)[C:5]([O:17][CH3:18])=[CH:4][N:3]=1.Cl.[NH2:20]O.C(=O)(O)[O-].[Na+].O>C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>[Cl:1][C:2]1[N:7]2[N:11]=[C:9]([NH2:20])[N:8]=[C:6]2[C:5]([O:17][CH3:18])=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 56949522Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

생성물 1

HCID 569495765-Chloro-8-methoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amine수율 69.6%

시약·촉매·용매 2

HCID 10340Sodium Carbonate촉매HCID 6342Acetonitrile용매

실험 절차

Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate (2) (290 mg, 1.0 mmol), hydroxylamine hydrochloride (143 mg, 2 eq), and sodium bicarbonate (170 mg, 2 eq) were combined. Water (5 mL) and acetonitrile (5 mL) were added at room temperature. The resulting slurry was stirred at room temperature overnight, then treated with 20 drops of saturated aqueous sodium carbonate solution. The resulting solution was sparged with nitrogen and cooled, producing the product as a chalky precipitate, which was collected by filtration (in two crops), washed with water, and dried to obtain the title compound as a solid (139 mg, 68%): mp 251° C.; 1H NMR (DMSO-d6) δ 7.73 (s, 1H), 3.98 (s 3H); 6.63 (s, 2H); 13C NMR (DMSO-d6): 166.30, 148.14, 128.91, 124.67, 57.51; Mass spec (accurate mass): Calcd for C6H6ClN5O 199.026087; found, 199.0256.

후처리

  1. customThe resulting solution was sparged with nitrogen
  2. temperaturecooled
  3. customproducing the product as a chalky precipitate, which
  4. filtrationwas collected by filtration (in two crops)
  5. washwashed with water
  6. customdried

출처 및 근거

ORD 기록
ord-78fb6dabb47843b1a72210c21b47e37e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338596B2

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