Ammonia → HCID 86689331、化合物

HRID 1504933ノート

反応式

HRID 1504933 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 86689331HCID 86689331、化合物収率 89%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30dd758acec24cdeaacdcc627e80d53e
出典データセット
uspto-grants-2015_12
特許番号
US09216958B2

反応ノート

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