tert-butyl N-(prop-2-yn-1-yl)carbamate → tert-Butyl 3-(2-amino-4-chloro-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate

HRID 2387792노트

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HRID 2387792 반응식
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].[Cl:12][C:13]1[C:18](I)=[C:17]([CH3:20])[N:16]=[C:15]([NH2:21])[N:14]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:21][C:15]1[N:14]=[C:13]([Cl:12])[C:18]([C:3]#[C:2][CH2:1][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[C:17]([CH3:20])[N:16]=1

참가 물질

4

반응물 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amine

생성물 1

HCID 86633394tert-Butyl 3-(2-amino-4-chloro-6-methylpyrimidin-5-yl)prop-2-ynylcarbamate수율 46.9%

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

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온도
70 °C

실험 절차

tert-Butyl prop-2-ynylcarbamate (3.11 g), 4-chloro-5-iodo-6-methylpyrimidin-2-amine (1.8 g) and bis(triphenylphosphine)palladium(II) chloride (0.469 g) were combined in TEA (100 mL). The reaction mixture was purged with nitrogen gas for 3 min then copper(I) iodide (0.254 g) added. The resulting mixture was stirred at 70° C. for 16 h, then cooled to rt and filtered. The filtrate was washed with water and brine, dried and the solvents evaporated. The crude material was dissolved in MeOH (20 mL), acidified with acetic acid (1 mL) and purified by SCX and further purified by chromatography eluting 10% MeOH and 0.25% Ammonia (7N) in DCM to afford the subtitle compound 0.93 g.

후처리

  1. customThe reaction mixture was purged with nitrogen gas for 3 min
  2. additioncopper(I) iodide (0.254 g) added
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. washThe filtrate was washed with water and brine
  6. customdried
  7. customthe solvents evaporated
  8. dissolutionThe crude material was dissolved in MeOH (20 mL)
  9. custompurified by SCX
  10. customfurther purified by chromatography
  11. washeluting 10% MeOH and 0.25% Ammonia (7N) in DCM

출처 및 근거

ORD 기록
ord-ce8b34d27d964b58a6fc7a7c1604ab2a
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268990B2

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