N,N'-Dicyclohexylurea → 1,4-Dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide

HRID 2351085ノート

反応式

HRID 2351085 の反応式
[O:1]=[C:2]1[C:7]([O:8]CC2C=CC=CC=2)=[CH:6][NH:5][C:4]([C:16]([NH:18][N:19]2[CH2:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])=[O:17])=[CH:3]1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.C(NC1CCCCC1)(NC1CCCCC1)=O>C(#N)C>[OH:8][C:7]1[C:2](=[O:1])[CH:3]=[C:4]([C:16]([NH:18][N:19]2[CH2:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])=[O:17])[NH:5][CH:6]=1

参加物

5

反応物 3

HCID 4277N,N'-DicyclohexylureaHCID 11708267BistrimethylsilylacetamidHCID 198480031,4-dihydro-4-oxo-5-(phenylmethoxy)-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridine-carboxamide

生成物 1

HCID 198480131,4-Dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a suspension of 1.71 g. (ca. 5 mmol) crude 1,4-dihydro-4-oxo-5-(phenylmethoxy)-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridine-carboxamide in 22 ml acetonitrile was added 4.1 g (20 mmol) bis(trimethylsilyl)acetamide. After stirring for 20 minutes the undissolved dicyclohexylurea was filtered off and 0.85 g palladium on carbon were added to the filtrate. After the mixture had been hydrogenated for one hour, the catalyst was removed by filtration and 2.1 ml methanol and 0.1 ml acetic acid were added to the filtrate. After stirring overnight the desired product was filtered off and dried in vacuo. Yield 0.7 g, melting point 285°-290° C. (dec.).

後処理

  1. additionTo a suspension of 1.71 g
  2. filtrationwas filtered off
  3. addition0.85 g palladium on carbon were added to the filtrate
  4. customthe catalyst was removed by filtration and 2.1 ml methanol and 0.1 ml acetic acid
  5. additionwere added to the filtrate
  6. filtrationwas filtered off
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-7f931630bbd84374a778080aa84c9a6e
出典データセット
uspto-grants-1989_10
特許番号
US04871841

反応ノート

読み込み中…