Triethylamine → 8-((4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)ethynyl)-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

HRID 920324

반응식

HRID 920324 반응식
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[CH:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[C:24]([F:27])([F:26])[F:25].Cl[C:29]1[CH:39]=[C:33]2[N:34]([CH3:38])[CH2:35][CH2:36][CH2:37][N:32]2[C:31](=[O:40])[N:30]=1>C1COCC1.CCOC(C)=O.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.[Cu]I>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]#[C:23][C:29]3[CH:39]=[C:33]4[N:34]([CH3:38])[CH2:35][CH2:36][CH2:37][N:32]4[C:31](=[O:40])[N:30]=3)=[CH:20][CH:21]=2)=[CH:11][C:10]=1[C:24]([F:25])([F:26])[F:27]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 717434718-Chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-oneHCID 866763761-Chloro-4-(4-ethynylphenoxy)-2-(trifluoromethyl)benzene

생성물 1

HCID 712365888-((4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)ethynyl)-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one수율 13%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A suspension of bis(triphenylphosphine)palladium(II) chloride (70.3 mg, 0.1 mmol) and copper(I) iodide (19.1 mg, 0.1 mmol) in anhydrous THF (12 mL), was purged with Ar for 10 mins at rt. The suspension was treated with triethylamine (0.42 mL, 3.0 mmol), and 1-chloro-4-(4-ethynylphenoxy)-2-(trifluoromethyl)benzene (446 mg, 1.5 mmol) was added under an Ar atmosphere, which produced a dark amber color. After 5 mins, 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (100 mg, 0.5 mmol) was added, and stirred for 2 h at 50° C. The reaction mixture was diluted with EtOAc, washed with water, and then concentrated. The residue was purified by MDAP to afford the title compound (30 mg) as a pale yellow solid.

후처리

  1. customwas purged with Ar for 10 mins at rt
  2. additionwas added under an Ar atmosphere, which
  3. customproduced a dark amber color
  4. washwashed with water
  5. concentrationconcentrated
  6. customThe residue was purified by MDAP

출처 및 근거

ORD 기록
ord-a660d1c907364c4685d67b3c06e8e494
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273054B2

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