Acetic Acid → 5-Bromo-1-methyl-3-(2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrazin-2(1H)-one

HRID 1919018ノート

反応式

HRID 1919018 の反応式
[Br:1][C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH2:17][NH:16][CH2:15][CH2:14]3)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:25](C)=O.[Na+].CC(O)=O.[OH-].[Na+]>CO>[Br:1][C:2]1[N:3]=[C:4]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH2:17][N:16]([CH3:25])[CH2:15][CH2:14]3)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 580437085-Bromo-1-methyl-3-(1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrazin-2(1H)-one

生成物 1

HCID 580436765-Bromo-1-methyl-3-(2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ylamino)pyrazin-2(1H)-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 221a (2.75 g, 7.5 mmol), formaldehyde (37% in H2O, 30 mL, 375 mmol), NaBH(OAc)3 (4.75 g, 22.5 mmol), and AcOH (25 ml, 150 mmol) in methanol (125 ml) was stirred for 4 hours at room temperature. The mixture was then brought to basic condition with saturated NaOH solution and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography eluting with 4:1 ethyl acetate/methanol to give 221b. (0.9 g, 34.4%) LC/MS: m/z 350 (M+H)+

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with 4:1 ethyl acetate/methanol

出典と根拠

ORDレコード
ord-0c2211ffed6945cfa239eb60bdef796a
出典データセット
uspto-grants-2013_12
特許番号
US08618107B2

反応ノート

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