Potassium Carbonate → 2-Amino-8-ethyl-4-methyl-6-(4-methyl-3-thienyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 886804ノート

反応式

HRID 886804 の反応式
O1CCOCC1.[NH2:7][C:8]1[N:9]=[C:10]([CH3:22])[C:11]2[CH:17]=[C:16](Br)[C:15](=[O:19])[N:14]([CH2:20][CH3:21])[C:12]=2[N:13]=1.[CH3:23][C:24]1[C:25](B(O)O)=[CH:26][S:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH2:7][C:8]1[N:9]=[C:10]([CH3:22])[C:11]2[CH:17]=[C:16]([C:25]3[C:24]([CH3:23])=[CH:28][S:27][CH:26]=3)[C:15](=[O:19])[N:14]([CH2:20][CH3:21])[C:12]=2[N:13]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 50839314-Methyl-3-thiopheneboronic acidHCID 576069632-amino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

生成物 1

HCID 161230642-Amino-8-ethyl-4-methyl-6-(4-methyl-3-thienyl)pyrido[2,3-d]pyrimidin-7(8H)-one収率 55%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A 3:1 solution of dioxane and water (4 mL) was added to a flask charged with 2-amino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (0.140 g, 0.495 mmol) from above, 4-methylthiophene-3-boronic acid (0.140 g, 0.989 mmol), Pd(PPh3)4 (0.057 mg, 0.050 mmol), and K2CO3 (0.205 g, 1.48 mmol). The flask was flushed with nitrogen and fitted with a reflux condenser and heated to 100° C. After 12 hours the reaction was cooled to room temperature and diluted with ethyl acetate (70 mL) and washed with water. The aqueous phase was separated and washed with an additional amount of ethyl acetate (70 mL). The organic phases were combined and washed with brine, separated and dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on SiO2 (1:1 methylene chloride:ethyl acetate) to give 2-Amino-8-ethyl-4-methyl-6-(4-methyl-3-thienyl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.081 g, 55% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6): δ 7.84 (s, 1H), 7.46 (d, J=4.0 Hz, 1H), 7.19 (m, 3H), 4.32 (q, J=8.0 Hz, 2H), 2.52 (s, 3H), 2.11 (bs, 3H), 1.19 (t, J=8.0 Hz, 3H); MS (EI) for C15H16N4OS: 301.1 (MH+).

後処理

  1. customThe flask was flushed with nitrogen
  2. customfitted with a reflux condenser
  3. temperatureAfter 12 hours the reaction was cooled to room temperature
  4. additiondiluted with ethyl acetate (70 mL)
  5. washwashed with water
  6. customThe aqueous phase was separated
  7. washwashed with an additional amount of ethyl acetate (70 mL)
  8. washwashed with brine
  9. customseparated
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified on SiO2 (1:1 methylene chloride:ethyl acetate)

出典と根拠

ORDレコード
ord-a6b9a9bc4622472aa56bb01aa94dc086
出典データセット
uspto-grants-2012_08
特許番号
US08247408B2

反応ノート

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