Potassium Carbonate → 3-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzaldehyde

HRID 1049915ノート

反応式

HRID 1049915 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[CH:13][N:14]=[C:15]([NH2:18])[C:16]=3[N:17]=2)[CH:5]=[CH:6][CH:7]=1.FC1C=C(B(O)O)C=C([CH:26]=[O:27])C=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[NH2:18][C:15]1[C:16]2[N:17]=[C:8]([C:4]3[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[CH:3]=3)[CH:26]=[O:27])[CH:9]=[CH:10][C:11]=2[N:12]=[CH:13][N:14]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 222791933-Fluoro-5-formylphenylboronic acidHCID 867039146-(3-Fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine

生成物 1

HCID 867039183-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzaldehyde収率 90%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A suspension of 6-chloropyrido[3,2-d]pyrimidin-4-amine (1) (3.61 g, 20 mmol), 3-fluoro-5-formylphenylboronic acid (CAS 328956-60-1) (4.03 g, 24 mmol, 1.2 eq), Pd(PPh3)4 (1.16 g, 1.0 mmol, 0.05 eq), and K2CO3 (5.53 g, 40 mmol, 2.0 eq) in a mixture of dioxane (100 mL) and H2O (10 mL) was heated at 100° C. for 3 h. After it was cooled to r.t., the reaction was extracted with EtOAc (100 mL) and water (60 mL). The organic layer were washed with water and concentrated. The yellow solid was recrystallized in MeCN to give the titled product (4.8 g, yield: 90%).

後処理

  1. temperatureAfter it was cooled to r.t.
  2. extractionthe reaction was extracted with EtOAc (100 mL) and water (60 mL)
  3. washThe organic layer were washed with water
  4. concentrationconcentrated
  5. customThe yellow solid was recrystallized in MeCN

出典と根拠

ORDレコード
ord-14d458fa545b4fc5a9defba99da2bef3
出典データセット
uspto-grants-2016_07
特許番号
US09382241B2

反応ノート

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