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

HRID 1049915노트

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HRID 1049915 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-14d458fa545b4fc5a9defba99da2bef3
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382241B2

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