Ammonia → 5-Bromo-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine

HRID 875943

반응식

HRID 875943 반응식
[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH3:16].C(OCC)(=O)C>C(O)(C)C>[Br:1][C:2]1[C:3]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:4][C:5]([NH2:16])=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 595508905-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine

생성물 1

HCID 582996735-Bromo-N4-(tetrahydro-pyran-4-yl)-pyrimidine-2,4-diamine수율 77%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
130 °C

실험 절차

To a suspension of compound 32 (6.60 g, 23 mmol) in isopropyl alcohol (40 ml) was added ammonia (aq. 28%, 80 ml). This reaction mixture was heated to 130° C. for 14 hours in a pressure vessel. The reaction mixture was cooled down to room temperature and to this mixture was added ethyl acetate. The reaction mixture was washed with water and brine. The ethyl acetate layer was dried with sodium sulfate and concentrated to give compound 33 (4.75 g, 77%). 1H NMR (500 MHz, CD3OD) δ ppm 7.79 (1 H, s), 4.24 (1 H, m), 3.99-4.02 (2 H, dd, J=11.0, 2.2 Hz), 3.52 (2 H, td, J=11.9, 2.0 Hz), 1.92-1.96 (2 H, m), 1.69 (2 H, m); LCMS-ESI (POS), M/Z, M+1: Found 273, Calculated 273.0

후처리

  1. temperatureThe reaction mixture was cooled down to room temperature and to this mixture
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialThe ethyl acetate layer was dried with sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4ed4a0daf9b74ca28c30c9bd6c07c2a6
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08980903B2

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