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Ethanol → 4-(2,4-Diamino-6-pyrimidyl)benzoic Acid Hydrochloride

HRID 352734
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HRID 352734 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.[C:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([OH:12])=[O:11].C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C>[ClH:1].[NH2:8][C:6]1[N:5]=[C:4]([NH2:9])[CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=2)[N:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 3121834-Carboxyphenylboronic Acid

생성물 1

HCID 694814324-(2,4-Diamino-6-pyrimidyl)benzoic Acid Hydrochloride수율 54%

시약·촉매·용매 4

HCID 178419050
HCID 178419050, 화합물
촉매
HCID 962Water용매2회
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

실험 절차

In toluene (9 ml), 6-chloro-2,4-diaminopyrimidine (434 mg) was dissolved, followed by the addition of 4-carboxyphenylboronic acid (667 mg), ethanol (2.5 ml), sodium carbonate (635 mg), water (3.0 ml) and bis(triphenylphosphine)palladium (II) dichloride (65 mg). The resulting mixture was heated under reflux for 24 hours under an argon gas atmosphere. Ethyl acetate and water were added to the reaction mixture. The water layer so separated was made acidic with 2N hydrochloric acid. The insoluble matter was collected by filtration, washed with water and tetrahydrofuran and then dried, whereby the title compound (371 mg, 54%) was obtained.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 24 hours under an argon gas atmosphere
  3. customThe water layer so separated
  4. filtrationThe insoluble matter was collected by filtration
  5. washwashed with water and tetrahydrofuran
  6. customdried

출처 및 근거

ORD 기록
ord-36c6ee1523fa451f9bdce4a6b5268834
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06747023B1

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