Hydrochloric Acid → 5-Amino-3-(cyclopropylmethoxy)pyrazine-2-carbonitrile

HRID 40660

反応式

HRID 40660 の反応式
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[NH2:8][C:9]1[N:10]=[C:11](Cl)[C:12]([C:15]#[N:16])=[N:13][CH:14]=1.Cl>O1CCOCC1>[NH2:8][C:9]1[N:10]=[C:11]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)[C:12]([C:15]#[N:16])=[N:13][CH:14]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 210753925-Amino-3-chloropyrazine-2-carbonitrile

生成物 1

HCID 596363535-Amino-3-(cyclopropylmethoxy)pyrazine-2-carbonitrile収率 83%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a solution of sodium hydride (93 mg, 3.882 mmol) in dioxane (4 mL) was added cyclopropylmethanol (280 mg, 3.882 mmol) dropwise. The solution was stirred for 30 minutes and then 5-amino-3-chloropyrazine-2-carbonitrile (300 mg, 1.941 mmol) was added and the reaction mixture heated at 90° C. for 14 hours. The reaction mixture was poured into aqueous HCl (1 M) and extracted with ethyl acetate. The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to dryness to give the title compound (305 mg, 1.605 mmol, 83%) which was used in subsequent steps without further purification. LC-MS (3) Rt=1.49 min; m/z (ESI+) 191 (M+H+).

後処理

  1. extractionextracted with ethyl acetate
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-99953e524ebb411787feb18a6c23ffa0
出典データセット
uspto-grants-2013_09
特許番号
US08530468B2

関連ノート

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