Water → HCID 178500481、化合物

HRID 982315ノート

反応式

HRID 982315 の反応式
I[N:2]1[C:7]([OH:8])=[C:6]2[CH:9]=[CH:10][N:11]=[C:5]2[N:4]=[CH:3]1.[C:12]([C:14]1[CH:33]=[CH:32][C:17]([C:18]([NH:20][C@H:21]([C:28]([O:30][CH3:31])=[O:29])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:19])=[CH:16][CH:15]=1)#[CH:13].C(N(CC)CC)C.O>CN(C)C=O.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:8][C:7]1[N:2]([C:13]#[C:12][C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:20][C@H:21]([C:28]([O:30][CH3:31])=[O:29])[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:19])=[CH:32][CH:33]=2)[CH:3]=[N:4][C:5]2=[N:11][CH:10]=[CH:9][C:6]=12

参加物

8

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 15024200Dimethyl 4-ethynylbenzoylglutamateHCID 178515134HCID 178515134、化合物

生成物 1

HCID 178500481HCID 178500481、化合物

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 10 mmol of 3-iodo-4-hydroxypyrrolo[2,3-d]pyrimidine in 40 mL of dimethylformamide are added 4.0 g (13.19 mmol) of dimethyl N-(4-ethynylbenzoyl)-L-glutamate, 0.38 g of copper (I) iodide, 3 mL of triethylamine, and 1.0 g of tetrakis(triphenylphosphine) palladium. This mixture is stirred at ambient temperatures for two hours and then poured into 500 mL of water. The solid is collected by filtration, air dried, and then refluxed in 200 mL of methanol. The mixture is cooled and the solid collected by filtration, dissolved in two liters of 10% methanol in methylene chloride. There is obtained dimethyl N-[4-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-ylethynyl)benzoyl]-L-glutamate which is purified by chromatography over silica, m.p. 160° C. (dec.). 1NMR (d6 -DMSO) δ1.98-2.15 (m, 2H), 2.45 (t, J=7.5 Hz, 2H), 3.57 (s, 3H), 3.64 (s, 3H), 4.40-4.45 (m, 1H), 7.51 ((d, J=2.5 Hz, 1H), 7.55 (d, J=8.2 Hz), 2H), 7.87 (s, 1H), 7.90 (d, J=8.2 Hz, 1H), 11.97 ((d, J=3.7 Hz, 1H), 12.31 (s, 1H).

後処理

  1. filtrationThe solid is collected by filtration, air
  2. customdried
  3. temperaturerefluxed in 200 mL of methanol
  4. temperatureThe mixture is cooled
  5. filtrationthe solid collected by filtration
  6. dissolutiondissolved in two liters of 10% methanol in methylene chloride

出典と根拠

ORDレコード
ord-051da07a907d4489ab58197aadc740f7
出典データセット
uspto-grants-1991_02
特許番号
US04996206

反応ノート

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