Ammonia → HCID 86689331, 화합물

HRID 1504933노트

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HRID 1504933 반응식
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([O:13][CH3:14])=[C:4](Cl)[N:3]=1.[NH3:16]>CS(C)=O.O>[NH2:16][C:4]1[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]=1[O:13][CH3:14]

참가 물질

5

반응물 2

HCID 222AmmoniaHCID 866893322,6-Dichloro-5-methoxy-4-furan-2-ylpyrimidine

생성물 1

HCID 86689331HCID 86689331, 화합물수율 89%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
60 °C

실험 절차

2,6-Dichloro-5-methoxy-4-furan-2-ylpyrimidine (500 mg, 2.0 mmol) (see Example 5 for the preparation of 2,6-dicholor-5-methoxy-4-furan-2-yl pyrimidine) was dissolved in dry DMSO (10 mL) and heated to 60° C. This mixture was treated with a gentle stream of ammonia. After approximately 2 h, conversion was complete to about a 95:5 ratio of mono-amino isomers (having a molar weight of 225 g/mol). This mixture was cooled and diluted with water (50 mL), and the product extracted with ethyl acetate (2×50 mL). Then, the product was washed with ethyl acetate, twice with water (25 mL), and once with saturated sodium chloride (25 mL). The result was dried and concentrated. The product was purified by column chromatography using silica with a 5 to 20% ramp of ethyl acetate/hexane to give the title compound (400 mg, 89% yield). The various isomers were not separated.

후처리

  1. temperatureThis mixture was cooled
  2. extractionthe product extracted with ethyl acetate (2×50 mL)
  3. washThen, the product was washed with ethyl acetate, twice with water (25 mL)
  4. customThe result was dried
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-30dd758acec24cdeaacdcc627e80d53e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216958B2

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