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1,3-Propanediol → 3-(2-(Dimethylamino)-5-pyrimidyl)aniline

HRID 1075455
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인쇄 미리보기

반응식

HRID 1075455 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[NH2:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CCO>O.C(COC)OC.C(OCC)(=O)C.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>[CH3:9][N:8]([CH3:10])[C:5]1[N:4]=[CH:3][C:2]([C:16]2[CH:17]=[C:12]([CH:13]=[CH:14][CH:15]=2)[NH2:11])=[CH:7][N:6]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 127353155-Bromo-N,N-dimethylpyrimidin-2-amine

생성물 1

HCID 538349803-(2-(Dimethylamino)-5-pyrimidyl)aniline수율 74%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매2회
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of 5-bromo-2-(dimethylamino)pyrimidine (6.76g, 33.17mmol), 3-aminophenylboronic acid hemisultat (7.4g, 39.78mmol) potassium carbonate (13.73g, 99.49mmol), 1,3-propanediol (12ml, 166mmol) and tetrakis(triphenylphosphine)palladium(0) (0.2g) in a mixture of water (30ml) and dimethoxyethane (60ml) is heated to 80° C. under nitrogen overnight. After cooling the mixture is diluted with water and ethyl acetate and is filtered through a fluted filterpaper. The layers are separated and the aqeous phase is extracted once with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated to dryness. The residue is triturated with a mixture of ethyl acetate and petroleum ether (1:1) to leave crystalline 2h (5.26g, 74%). Mp 115.5-117° C.

후처리

  1. temperatureAfter cooling the mixture
  2. filtrationis filtered through a fluted filterpaper
  3. customThe layers are separated
  4. extractionthe aqeous phase is extracted once with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue is triturated with a mixture of ethyl acetate and petroleum ether (1:1)

출처 및 근거

ORD 기록
ord-7570d669382c40e982bb85241a1119a2
출처 데이터셋
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05902813

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