Triethylamine → 2-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid

HRID 871874

반응식

HRID 871874 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[NH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15].C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:12][CH2:13][C:14]([OH:16])([CH3:17])[CH3:15])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 951022-Propanol, 1-amino-2-methyl-HCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acid

생성물 1

HCID 866731432-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid수율 59.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
3.5 °C

실험 절차

A suspension of 19.9 g (86.73 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid in 155 mL of THF is cooled on an ice bath to 2-5°C., and a solution of 8.5 g (95.40 mmol) of 1-amino-2-methyl-2-propanol and 36.3 mL (260.19 mmol) of triethylamine in 60 mL of THF is added dropwise. The mixture is stirred at room temperature overnight. Ethyl acetate and water are added. After separation of the phases by settling, the aqueous phase is acidified with aqueous 1N HCl solution to pH 2. The precipitate is isolated by filtration to give 12.6 g of the expected product in the form of a pale yellow solid, which is used as obtained in the following step. Yield=59%.

후처리

  1. customAfter separation of the phases
  2. customThe precipitate is isolated by filtration

출처 및 근거

ORD 기록
ord-f1b8463a504b4795b4911c5acf111e44
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975250B2

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