Dimethylacetamide → 2-Amino-4-cyano-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 1161752노트

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HRID 1161752 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

HCID 595193422-Amino-4-cyano-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

시약·촉매·용매 4

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

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-03a2198650744cf0b03645c84c4583b0
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820658B2

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