Triethylamine → 2-Chloro-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyrimidine

HRID 1360814노트

반응식

HRID 1360814 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH3:9][C:10]1[S:11][CH:12]=[C:13]([C:15]#[CH:16])[N:14]=1.C(N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:16]#[C:15][C:13]2[N:14]=[C:10]([CH3:9])[S:11][CH:12]=2)=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 116223344-Ethynyl-2-methyl-1,3-thiazole

생성물 1

HCID 578230292-Chloro-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyrimidine

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매

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온도
60 °C

실험 절차

2-Chloro-5-bromopyrimidine (5.0 g, 26 mmol), 2-methyl-4-ethynyl-1,3-thiazole (3.2 g, 26 mmol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol), copper(I) iodide (0.1 g, 0.5 mmol) and triethylamine (13 g, 130 mmol) were added to deoxygenated toluene (50 mL) at room temperature. The reaction was then warmed to 60° C. Stirring continued for 2.5 hrs and the reaction contents were then poured in to a separatory funnel and partitioned with EtOAc (100 mL) and water (100 mL). The organic layer was then washed with water twice (250 mL each). The organic layer were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was chromatographed on SiO2, eluting with 1:1 EtOAc:hexanes to afford 2-chloro-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyrimidine as a tan solid. 1H-NMR (CDCl3, 300 MHz) δ 8.78 (s, 2H), 7.52 (s, 1H), 2.78 (s, 3H).

후처리

  1. customto deoxygenated toluene (50 mL) at room temperature
  2. customthe reaction contents
  3. additionwere then poured in to a separatory funnel
  4. custompartitioned with EtOAc (100 mL) and water (100 mL)
  5. washThe organic layer was then washed with water twice (250 mL each)
  6. dry with materialThe organic layer were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was chromatographed on SiO2
  10. washeluting with 1:1 EtOAc

출처 및 근거

ORD 기록
ord-a7a4b315fb5844b0beafb8fc143c7f6c
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879882B2

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