Triethylamine → Carbonic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester Ethyl Ester

HRID 705578노트

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HRID 705578 반응식
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.C(N(CC)CC)C.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(Cl)Cl>[CH2:25]([O:24][C:22](=[O:23])[O:8][C:5]1[N:4]=[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])[C:2]([F:1])=[CH:7][N:6]=1)[CH3:26]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178484257HCID 178484257, 화합물

생성물 1

HCID 57818850Carbonic Acid 4-(dimethylamino-methyleneamino)-5-fluoropyrimidin-2-yl Ester Ethyl Ester수율 22.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (0.10, 0.54 mmol) in CH2Cl2 (2 mL) were added triethylamine (0.20 g, 2.0 mmol) and ethyl chloroformate (0.065 g, 0.60 mmol), and the mixture was agitated on an orbital shaker at room temperature overnight. The reaction was diluted with CH2Cl2 and the solution was washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by silica gel column chromatography (EtOAc/petroleum ether gradient) to yield 0.031 g (22%) of the title compound as a white solid: mp 124-126° C.; 1H NMR (300 MHz, CDCl3) δ 8.67 (s, 1H), 8.19 (d, J=2.2 Hz, 1H), 4.35 (q, J=7.14 Hz, 2H), 3.21 (s, 6H), 1.40 (t, J=7.14 Hz, 3H); HPLC-MS (ESI) m/z 258 (M+H)+.

후처리

  1. washthe solution was washed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by silica gel column chromatography (EtOAc/petroleum ether gradient)

출처 및 근거

ORD 기록
ord-78912ea571e343edbb101a4b84c8528b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174970B2

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