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 379597노트

반응식

HRID 379597 반응식
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

참가 물질

8

반응물 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, 화합물

생성물 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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-246432ae8a2143ac89c7d1ec356022c8
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300334B1

반응 노트

불러오는 중…