4-Amino-6-chloropyrimidine → N-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-pyrimidine-4,6-diamine

HRID 409654노트

반응식

HRID 409654 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[N:9]1([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>O.C(O)(=O)C>[N:9]1([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:2]3[CH:3]=[C:4]([NH2:8])[N:5]=[CH:6][N:7]=3)=[CH:20][CH:19]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

참가 물질

5

반응물 2

HCID 2380124-Amino-6-chloropyrimidineHCID 64847114-(2-Morpholinoethoxy)aniline

생성물 1

HCID 59864576N-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-pyrimidine-4,6-diamine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-chloro-pyrimidin-4-ylamine (194 mg, 1.5 mmol, 1.3 equiv), 4-(2-morpholin-4-yl-ethoxy)-phenylamine (256 mg, 1.15 mmol) in H2O (1 mL) and glacial acetic acid (5 mL) is stirred for 16 h at 100° C. After solvent evaporation, the residue is taken up in DCM and diluted with a saturated aqueous solution of NaHCO3. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is triturated in EtOAc to provide the title compound as a grey solid: ESI-MS: 316.2 [MH]+; tR=1.00 min (purity: 95%, system 1); TLC: Rf=0.22 (DCM/MeOH+1% NH3aq, 93:7).

후처리

  1. customAfter solvent evaporation
  2. additiondiluted with a saturated aqueous solution of NaHCO3
  3. customThe aqueous layer is separated
  4. extractionextracted with DCM
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is triturated in EtOAc

출처 및 근거

ORD 기록
ord-71a74807b003482ca13a3ede60901537
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759517B2

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