Water → 6-(Bromomethyl)thieno[3,2-b]pyrazine

HRID 1184860ノート

反応式

HRID 1184860 の反応式
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([CH2:10]O)=[CH:9][C:2]=12.P(Br)(Br)[Br:13].O.[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Br:13][CH2:10][C:8]1[S:7][C:3]2[C:2](=[N:1][CH:6]=[CH:5][N:4]=2)[CH:9]=1

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 67125540Thieno[2,3-b]pyrazin-6-ylmethanol

生成物 1

HCID 671255506-(Bromomethyl)thieno[3,2-b]pyrazine収率 63.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of thieno[3,2-b]pyrazin-6-ylmethanol 87 (408 mg, 2.455 mmol) in CH2Cl2 (8 mL) and THF (8 mL) was added phosphorus tribromide (1/166 mL, 12.27 mmol) and stirred overnight at rt. Water was added, alkalized with 2N NaOH and extracted with EtOAc. Organic layer was washed with NaHCO3 (aq) solution, brine, dried and evaporated. Purification by chromatography (CH2CL2) gave pure 6-(bromomethyl)thieno[3,2-b]pyrazine 47 (356 mg, 63%). NMR (400 MHz, CDCl3) 4.80 (s, 2H), 7.71 (s, 1H), 8.49 (d, J=2.3 Hz, 1H), 8.64 (d, J=2.3 Hz, 1H). (m/z)=229 and 231 (M+H)+.

後処理

  1. extractionextracted with EtOAc
  2. washOrganic layer was washed with NaHCO3 (aq) solution, brine
  3. customdried
  4. customevaporated
  5. customPurification by chromatography (CH2CL2)

出典と根拠

ORDレコード
ord-41b48f1c844b4fc88f92fdcaca56d5da
出典データセット
uspto-grants-2014_03
特許番号
US08669256B2

反応ノート

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