Dimethylacetamide → HCID 59519342、化合物

HRID 237398

反応式

HRID 237398 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:16][C:9]2[N:10]=[C:11]([NH2:15])[N:12]=[C:13](Cl)[C:8]=2[CH:7]=1)=[O:5])[CH3:2].C[C:18]([N:20](C)C)=O>[C-]#N.[C-]#N.[Zn+2].[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[S:16][C:9]2[N:10]=[C:11]([NH2:15])[N:12]=[C:13]([C:18]#[N:20])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

参加物

7

反応物 2

HCID 31374DimethylacetamideHCID 16096301Ethyl 2-amino-4-chlorothieno(2,3-d)pyrimidine-6-carboxylate

生成物 1

HCID 59519342HCID 59519342、化合物

試薬・触媒・溶媒 4

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 23994Zinc触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
120 °C

実験手順

2-Amino-4-chloro-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (1 equiv.), Zn(CN)2 (0.6 equiv.), Zn dust (0.12 equiv.), Pd2(dba)3 (0.02 mole eq.) and 1,1′-bis(diphenylphosphino)ferrocene (0.04 equiv.) were mixed in DMA and the mixture was stirred under argon at 120° C. for 24 hours. The resulting suspension was filtered through a short Celite column, the filtrate was diluted with brine and extracted with ethyl acetate. The organic layer was then washed with brine, water and dried over sodium sulphate. After evaporation of the solvent, the crude oil was purified by preparative TLC.

後処理

  1. filtrationThe resulting suspension was filtered through a short Celite column
  2. additionthe filtrate was diluted with brine
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was then washed with brine, water
  5. dry with materialdried over sodium sulphate
  6. customAfter evaporation of the solvent
  7. customthe crude oil was purified by preparative TLC

出典と根拠

ORDレコード
ord-8ac7a9a78b8c4221be440008c345952c
出典データセット
uspto-grants-2014_02
特許番号
US08642594B2

関連ノート

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