(E)-trimethyl(2-(tributylstannyl)vinyl)silane → HCID 68150547、化合物

HRID 244311ノート

反応式

HRID 244311 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]=1Br.[CH3:17][Si:18]([CH3:35])([CH3:34])/[CH:19]=[CH:20]/[Sn](CCCC)(CCCC)CCCC>O1CCOCC1.C(OCC)(=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]=1/[CH:20]=[CH:19]/[Si:18]([CH3:35])([CH3:34])[CH3:17]

参加物

7

反応物 2

HCID 10949136(E)-trimethyl(2-(tributylstannyl)vinyl)silaneHCID 11414935HCID 11414935、化合物

生成物 1

HCID 68150547HCID 68150547、化合物収率 57.2%

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

Ethyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate (0.5 g, 1.747 mmol, see WO 2005063721 for preparation) and tetrakis (triphenylphosphine) palladium(0) (0.214 g, 0.185 mmol) were added to a 20 mL Biotage microwave reaction vessel. The vessel was sealed and purged with nitrogen gas. (E)-trimethyl(2(tributylstannyl)vinyl)silane (0.96 g, 2.466 mmol) in dioxane (8.74 ml) was added and the reaction mixture was heated at 120° C. for 6 h. The cooled reaction mixture was diluted with ethyl acetate and water. The organic phase was washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated onto silica. Purification by flash chromatography (SiO2, 0-40% EtOAc:Hex gradient) provided the title compound as a tan solid (0.305 g, 57% yield): mp 99-101° C.; 1H NMR (400 MHz, DMSO-d6) δ 0.12 (s, 9H), 0.85-0.94 (m, 4H), 1.25 (t, J=7.1 Hz, 3H), 1.91 (tt, J=7.0, 5.6 Hz, 1H), 4.20 (q, J=7.1 Hz, 2H), 6.03 (d, J=19.1 Hz, 1H), 6.70 (d, J=19.2 Hz, 1H), 7.01 (s, 2H); ESIMS m/z 306 ([M+H]+), 304 ([M−H]−).

後処理

  1. customThe vessel was sealed
  2. custompurged with nitrogen gas
  3. customThe cooled reaction mixture
  4. washThe organic phase was washed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated onto silica
  8. customPurification by flash chromatography (SiO2, 0-40% EtOAc:Hex gradient)

出典と根拠

ORDレコード
ord-7b2afb77a99149a384ee2b4c64046f20
出典データセット
uspto-grants-2014_02
特許番号
US08658568B2

反応ノート

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