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

HRID 885027ノート

反応式

HRID 885027 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-028f6beb86f645d4823bdb4877c5278c
出典データセット
uspto-grants-2012_08
特許番号
US08242143B2

反応ノート

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