Sodium Iodide → (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine

HRID 491360

반응식

HRID 491360 반응식
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[NH2:15][C:16]1[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=1.C(N(CC)CC)C.[I-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:15][C:16]2[NH:17][N:18]=[C:19]([CH3:21])[CH:20]=2)[CH:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 2415542,4-Dichloro-6-phenylpyrimidine

생성물 1

HCID 178418761(2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine수율 62.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

To a solution of 2,4-dichloro-6-phenyl-pyrimidine (300 mg, 1.33 mmol) and 3-amino-5-methylpyrazole (129 mg, 1.33 mmol) in DMF (7 mL) is added triethylamine (195 μL, 1.40 mmol) followed by sodium iodide (200 mg, 1.33 mmol) and the reaction mixture is stirred for 15 hours at 90° C. The resulting solution is partitioned between ethyl acetate and water and the organic phase washed with brine, dried over MgSO4 then concentrated in vacuo. The residue is triturated in methanol and the resulting white solid collected by filtration to afford (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (236 mg, 62%).

후처리

  1. customThe resulting solution is partitioned between ethyl acetate and water
  2. washthe organic phase washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationthen concentrated in vacuo
  5. customThe residue is triturated in methanol
  6. filtrationthe resulting white solid collected by filtration

출처 및 근거

ORD 기록
ord-d9645d242ebb4dbebbc06ce945ec149b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531536B2

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