Ammonium Chloride → 6[Hydroxy[6-(trifluoromethyl)-2-pyridinyl]methyl]-3-methyl-1-(2-methylpropyl)-5-(2-thienylthio)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 379597ノート

反応式

HRID 379597 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[N:8]=1.[CH3:17][N:18]1[C:23](=[O:24])[C:22]2[C:25]([S:30][C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)=[C:26]([CH:28]=[O:29])[S:27][C:21]=2[N:20]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:19]1=[O:40].[Li]C1C=CC=CN=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[OH:29][CH:28]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[N:8]=1)[C:26]1[S:27][C:21]2[N:20]([CH2:36][CH:37]([CH3:39])[CH3:38])[C:19](=[O:40])[N:18]([CH3:17])[C:23](=[O:24])[C:22]=2[C:25]=1[S:30][C:31]1[S:32][CH:33]=[CH:34][CH:35]=1

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 27829022-Bromo-6-(trifluoromethyl)pyridineHCID 183665901,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(thien-2-ylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehydeHCID 178418339ButyllithiumHCID 178506720HCID 178506720、化合物

生成物 1

HCID 101866156[Hydroxy[6-(trifluoromethyl)-2-pyridinyl]methyl]-3-methyl-1-(2-methylpropyl)-5-(2-thienylthio)-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

n-Butyl lithium in hexane (2.5M, 369 μl) was added dropwise to a solution of 2-bromo-6-trifluoromethylpyridine in tetrahydrofuran (8 ml) at −78° C. and the resulting solution was stirred for 1 h. 1,2,3,4-Tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-5-(2-thienylthio)-thieno[2,3-d]pyrimidine-6-carboxaldehyde (0.25 g) (Example 50, step c) in tetrahydrofuran (2 ml) was added dropwise to the lithio pyridine solution. The reaction was stirred for 3 hours at −78° C. then saturated ammonium chloride solution was added (20 ml) and the reaction was left to warm to room temperature. The reaction was extracted thrice with ethyl acetate (50 ml), then the organic phases were washed with brine and dried over magnesium sulfate, filtered and evaporated to leave a brown oil. The residue was purified by chromatography (1:4, ethyl acetate: isohexane) to give the title compound as a pale brown oil (0.03 g).

後処理

  1. stirringThe reaction was stirred for 3 hours at −78° C.
  2. waitthe reaction was left
  3. extractionThe reaction was extracted thrice with ethyl acetate (50 ml)
  4. washthe organic phases were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto leave a brown oil
  9. customThe residue was purified by chromatography (1:4, ethyl acetate: isohexane)

出典と根拠

ORDレコード
ord-246432ae8a2143ac89c7d1ec356022c8
出典データセット
uspto-grants-2001_10
特許番号
US06300334B1

反応ノート

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