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Ammonium Chloride → t-Butyl [3-(4,6-dimethoxypyrimidin-2-ylmethyl)-2-pyridyl]carbamate

HRID 1418817
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HRID 1418817 반응식
C([Li])CCC.[CH3:6][C:7]1[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1.[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([CH2:6][C:7]2[C:8]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[N:9][CH:10]=[CH:11][CH:12]=2)[N:24]=1
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참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 117458482-(N-Boc-Amino)-3-methylpyridineHCID 178418339Butyllithium

생성물 1

HCID 53782638t-Butyl [3-(4,6-dimethoxypyrimidin-2-ylmethyl)-2-pyridyl]carbamate

시약·촉매·용매 2

HCID 8028
Tetrahydrofuran
용매
HCID 8058Hexane용매

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온도
-70 °C

실험 절차

n-Butyllithium (19.2 ml of a 2.5M solution in hexane) was added dropwise to a stirred suspension of the product of stage (a) above (5.0 g) in dry tetrahydrofuran (100 ml) under nitrogen at -70° C. The mixture was stirred at -70° C. for 20 minutes and then at 5° C. for 3 hours. It was then cooled to -70° C. and treated with 4,6-dimethoxy-2-methylsulfonylpyrimidine (5.42 g), and the mixture was stirred at -70° C. for 1 hour, then at room temperature overnight. Saturated ammonium chloride solution (500 ml) was added, and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with saturated sodium chloride solution (50 ml), dried and evaporated to give an orange oil which was triturated with hexane to give 5.35 g of the desired product as a pale yellow solid, mp 89°-92° C.

후처리

  1. waitat 5° C. for 3 hours
  2. temperatureIt was then cooled to -70° C.
  3. stirringthe mixture was stirred at -70° C. for 1 hour
  4. customat room temperature
  5. customovernight
  6. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  7. washThe combined extracts were washed with saturated sodium chloride solution (50 ml)
  8. customdried
  9. customevaporated
  10. customto give an orange oil which
  11. customwas triturated with hexane

출처 및 근거

ORD 기록
ord-3dfb63236e5942579a342a0ca48fa300
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05885935

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