Triethylamine → 5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine

HRID 421996

반응식

HRID 421996 반응식
Cl[C:2]1[C:7]([I:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.C(N(CC)CC)C.Cl.[NH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CCO.O>[I:8][C:7]1[C:2]([NH:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:3][C:4]([NH2:10])=[N:5][C:6]=1[CH3:9]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amineHCID 441186934-Aminotetrahydropyran hydrochloride

생성물 1

HCID 592727355-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine수율 51.7%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a suspension of 4-chloro-5-iodo-6-methylpyrimidin-2-amine (16.0 g, 59.3 mmol) in EtOH (200 mL) and H2O (250 mL) was added triethylamine (30.0 mL, 207.5 mmol) and 4-aminotetrahydropyran HCl salt (9.75 g, 71.2 mmol) successively. The reaction was heated to reflux, stirred for 72 h, and then cooled to RT. About 80% of the solvent was evaporated under reduced pressure. The mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the crude product. The product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate) to afford 5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine as a light yellow crystal (yield: 10.23 g, 51.7%). LC/MS: calculated for C10H15IN4O (334.03). found: 335.08 (MH+). HPLC analytical purity: >99.0%.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customAbout 80% of the solvent was evaporated under reduced pressure
  4. customThe mixture was partitioned between ethyl acetate and H2O
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product
  8. customThe product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate)

출처 및 근거

ORD 기록
ord-2ca2efa525ca4b29b8ac6868fb6fd18a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101622B2

연결된 노트

불러오는 중…