Acetic Acid → 6-Bromo-2-(2-cyclopropyl-4-pyrimidinyl)-1h-imidazo[4,5-b]pyrazine

HRID 931231ノート

反応式

HRID 931231 の反応式
[Br:1][C:2]1[N:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[CH:10]1([C:13]2[N:18]=[C:17]([C:19](=N)OCC)[CH:16]=[CH:15][N:14]=2)[CH2:12][CH2:11]1.C(N(CC)CC)C.C(O)(=O)C>C(O)C>[Br:1][C:2]1[N:3]=[C:4]2[NH:9][C:19]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([CH:10]4[CH2:12][CH2:11]4)[N:18]=3)=[N:8][C:5]2=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 27718575-Bromopyrazine-2,3-diamineHCID 89854162Ethyl 2-cyclopropylpyrimidine-4-carbimidate2 回

生成物 1

HCID 898533786-Bromo-2-(2-cyclopropyl-4-pyrimidinyl)-1h-imidazo[4,5-b]pyrazine収率 25%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 5-bromopyrazine-2,3-diamine (50 mg, 0.3 mmol) and ethyl 2-cyclopropylpyrimidine-4-carbimidate (Intermediate 19, 50.7 mg, 0.3 mmol), triethylamine (73.8 μL, 0.5 mmol), acetic acid (244 μL, 4.2 mmol) and ethanol (0.8 mL) was heated to 100° C. for 30 min. The mixture was concentrated and diluted with water. Then a saturated aqueous solution of sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The organics were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude material was purified via flash chromatography (0-5% methanol in dichloromethane) to afford 6-bromo-2-(2-cyclopropylpyrimidin-4-yl)-1H-imidazo[4,5-b]pyrazine (21 mg, 25%).

後処理

  1. concentrationThe mixture was concentrated
  2. additiondiluted with water
  3. additionThen a saturated aqueous solution of sodium bicarbonate was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified via flash chromatography (0-5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-9bc4a801e7794d64b45e16619e18ba17
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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