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

HRID 1669652노트

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HRID 1669652 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

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온도
72 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0272ddaf30ba43408e948cdbc1af6007
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989620B2

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