Dimethylformamide → (5S)-5-({[4-[(2-Cyclopropylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)-5-methylimidazolidine-2,4-dione

HRID 1669652ノート

反応式

HRID 1669652 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]([CH:8]2[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:11]([C:13]1[CH2:14][CH2:15][N:16]([S:19]([CH2:22]N2C(C)C(=O)NC2=O)(=[O:21])=[O:20])[CH2:17][CH:18]=1)#[CH:12].[CH3:31][CH2:32][N:33](CC)CC.C[N:39]([CH:41]=[O:42])[CH3:40].C1C[O:46]CC1>[Cu]I.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>[CH:8]1([C:5]2[N:4]=[CH:3][C:2]([C:12]#[C:11][C:13]3[CH2:14][CH2:15][N:16]([S:19]([CH2:22][C@@:32]4([CH3:31])[NH:33][C:40](=[O:46])[NH:39][C:41]4=[O:42])(=[O:20])=[O:21])[CH2:17][CH:18]=3)=[CH:7][N:6]=2)[CH2:10][CH2:9]1

参加物

8

反応物 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 204444135-Bromo-2-cyclopropylpyrimidineHCID 86642353{[(4-ethynyl-3,6-dihydropyridin-1(2H)-yl)sulfonyl]methyl}-5-methylimidazolidine-2,4-dione

生成物 1

HCID 11553444(5S)-5-({[4-[(2-Cyclopropylpyrimidin-5-yl)ethynyl]-3,6-dihydropyridin-1(2H)-yl]sulfonyl}methyl)-5-methylimidazolidine-2,4-dione

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
72 °C

実験手順

The title compound was prepared following the general method of Yamanaka et al, Synth. Commun., 1983, 312-314. To 5-bromo-2-cyclopropylpyrimidine (110 mg, 0.55 mmol) and (5S)-5-({[(4-ethynyl-3,6-dihydropyridin-1(2H) -yl)sulfonyl]methyl}-5-methylimidazolidine-2,4-dione (180 mg, 0.61 mmol) in THF (3 mL) was added Et3N (1 mL) and DMF (1 mL) at 35° C. After a solution was formed, CuI (4 mol %) and PdCl2(PPh3)2 (2 mol %) were added and the mixture was heated at 72° C. for 6 hours. The mixture was partitioned between EtOAc (15 mL) and water (10 mL), and the aqueous layer was extracted three times with EtOAc. The combined organic layers were dried and concentrated to give the crude product as a yellow oil. The title compound (65 mg) was obtained by purification using preparative HPLC.

後処理

  1. customAfter a solution was formed
  2. customThe mixture was partitioned between EtOAc (15 mL) and water (10 mL)
  3. extractionthe aqueous layer was extracted three times with EtOAc
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customto give the crude product as a yellow oil

出典と根拠

ORDレコード
ord-0272ddaf30ba43408e948cdbc1af6007
出典データセット
uspto-grants-2011_08
特許番号
US07989620B2

反応ノート

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