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

HRID 1668829ノート

反応式

HRID 1668829 の反応式
[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

参加物

9

反応物 5

HCID 947Nitrogen2 回HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2313312,4-dichloro-5H,6H,7H-cyclopenta(d)pyrimidineHCID 668614323,5-Dimethyl-isoxazoleboronic acid

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
27.5 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2ba438119aa04ebb87a31aa3afc2cb71
出典データセット
uspto-grants-2011_08
特許番号
US07989463B2

反応ノート

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