Triethylamine → 4-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acid

HRID 871860

반응식

HRID 871860 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].C(OCC)(=O)C>C1COCC1>[C:26]([O:25][C:24]([NH:23][CH2:22][CH2:21][CH2:20][NH:19][C:6]1[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)=[O:30])([CH3:29])([CH3:28])[CH3:27]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acid

생성물 1

HCID 866731374-(3-tert-Butoxycarbonylaminopropylamino)-2-chloropyrimidine-5-carboxylic acid수율 88.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2.21 g (11.45 mmol) of 2,4-dichloro-5-pyrimidinecarboxylic acid prepared in step 2.3 (method B) in 20 mL of anhydrous THF is cooled to 2-5°C. on an ice bath. A solution of 4.79 mL (34.35 mmol) of triethylamine and 2 g (11.48 mmol) of tert-butyl (3-aminopropyl)carbamate in 15 mL of anhydrous THF is then added dropwise. The reaction mixture is stirred at room temperature for 30 minutes. Ethyl acetate is added and the organic phase is washed with aqueous 1N HCl and with water. The organic phases are combined, dried over sodium sulfate, filtered and concentrated under vacuum. 3.35 g of the expected product are obtained in the form of a yellow solid. Yield=88.6%.

후처리

  1. washthe organic phase is washed with aqueous 1N HCl and with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-1a9afc175b754b5ea5efbc5e0b1ac308
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975250B2

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