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

HRID 1075455
ノート
印刷プレビュー

反応式

HRID 1075455 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

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

生成物 1

HCID 538349803-(2-(Dimethylamino)-5-pyrimidyl)aniline収率 74%

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒2 回
HCID 80711,2-Dimethoxyethane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7570d669382c40e982bb85241a1119a2
出典データセット
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05902813

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート