4-(Morpholinomethyl)aniline → 5-Methyl-N2-(4-morpholin-4-ylmethyl-phenyl)-pyrimidine-2,4-diamine

HRID 491201

반응식

HRID 491201 반응식
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH3:9])=[CH:4][N:3]=1.[N:10]1([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>C(O)(=O)C>[CH3:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([CH2:16][N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)=[CH:22][CH:21]=2)=[N:3][CH:4]=1

참가 물질

4

반응물 2

HCID 7768514-(Morpholinomethyl)anilineHCID 43021752-Chloro-5-methylpyrimidin-4-amine

생성물 1

HCID 576751245-Methyl-N2-(4-morpholin-4-ylmethyl-phenyl)-pyrimidine-2,4-diamine수율 83.5%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
70 °C

실험 절차

A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.40 g, 2.8 mmol) and 4-morpholin-4-ylmethyl-phenylamine (0.60 g, 3.1 mmol) in acetic acid (15 mL) was heated at 70° C. for 17 h. After cooling to room temperature, the mixture was concentrated. The residue was taken in water (30 mL) and neutralized with 10% NaOH solution until pH ˜10. The resulting aqueous layer was extracted with EtOAc (2×30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated to afford the title compound as a brown syrup (0.70 g, 83%). It was used in the next step without purification. MS (ES+): m/z 300 (M+H)+.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. extractionThe resulting aqueous layer was extracted with EtOAc (2×30 mL)
  4. washthe combined organic layers washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-1a433620711d442b99af4708d134dc86
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528143B2

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