4-Aminophenol → 4-(6-Fluoropyrimidin-4-yloxy)benzenamine

HRID 1993545

반응식

HRID 1993545 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[F:13][C:14]1[CH:19]=[C:18](F)[N:17]=[CH:16][N:15]=1>O1CCOCC1>[F:13][C:14]1[N:15]=[CH:16][N:17]=[C:18]([O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH:19]=1

참가 물질

6

반응물 4

HCID 4034-AminophenolHCID 24758Sodium hydrideHCID 1377174,6-DifluoropyrimidineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 586594294-(6-Fluoropyrimidin-4-yloxy)benzenamine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매2회

실험 절차

4-Amino-phenol (0.135 g, 1.21 mmol) is added in one portion to a suspension of NaH (60% free-flowing powder moistened with oil, 58.2 mg, 1.45 mmol, 1.2 equiv) in dioxane abs. (1.4 mL), under an argon atmosphere. When hydrogen evolution subsides, a solution of 4,6-difluoro-pyrimidine (0.141 g, 1.21 mmol) in dioxane (0.4 mL) Is added. The resulting dark mixture is stirred for 1.5 h at rt, quenched by addition of MeOH (2 mL) and concentrated in vacuo. After addition of CH2Cl2, the resulting suspension is filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography (CH2Cl2/Et2O, 90/10, then 85/15) to afford the title compound as a white solid: ES-MS: 204.0 [M+H]+; single peak at tR=4.96 min (System 2); Rf=0.30 (CH2Cl2/Et2O, 85/15).

후처리

  1. customquenched by addition of MeOH (2 mL)
  2. concentrationconcentrated in vacuo
  3. additionAfter addition of CH2Cl2
  4. filtrationthe resulting suspension is filtered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography (CH2Cl2/Et2O, 90/10

출처 및 근거

ORD 기록
ord-d938ce83a85d4291b07a4f2181d2b472
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652022B2

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