Nitrogen → 2-chloro-4-(3,5-dimethyl-isoxazol-4-yl)-6,7-dihydro-5H-cyclopentapyrimidine

HRID 1668829노트

반응식

HRID 1668829 반응식
[CH3:1][C:2]1(B(O)O)[CH:6]=[C:5]([CH3:7])[O:4][NH:3]1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]2[CH2:19][CH2:20][CH2:21][C:14]=2[N:13]=1.N#N.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:11][C:12]1[N:17]=[C:16]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:7])[C:15]2[CH2:19][CH2:20][CH2:21][C:14]=2[N:13]=1

참가 물질

9

반응물 5

HCID 947Nitrogen2회HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidineHCID 668614323,5-Dimethyl-isoxazoleboronic acid

생성물 1

HCID 593628852-chloro-4-(3,5-dimethyl-isoxazol-4-yl)-6,7-dihydro-5H-cyclopentapyrimidine수율 74.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
27.5 °C

실험 절차

3,5-Dimethylisoxazole boronic acid (0.4 g, 2.8 mmol) was added to a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopentapyrimidine (0.75 g, 4 mmol) in tetrahydrofuran (10 mL). The mixture was flushed with N2 before addition of palladium acetate (0.07 g, 0.28 mmol) and triphenylphosphine (0.14 g, 0.56 mmol). Thereafter, 2M aqueous sodium carbonate solution was added and the mixture was reflushed with N2. The mixture was stirred at a temperature in the range of 20° C. to 50° C. for 8 to 12 hours and then cooled to about 20 to 35° C. The mixture was diluted with water and the organic layer was separated. The aqueous layer was re-extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel) to afford the title compound as a light yellow liquid (0.52 g, 53% yield).

후처리

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by column chromatography (silica gel)

출처 및 근거

ORD 기록
ord-2ba438119aa04ebb87a31aa3afc2cb71
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989463B2

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