Dimethylformamide → 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide

HRID 1041404노트

반응식

HRID 1041404 반응식
[NH2:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][C:8]#[CH:9])=[O:5].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[N:31]=[C:30](Cl)[C:29]([Cl:33])=[CH:28][N:27]=1>>[Cl:25][C:26]1[N:31]=[C:30]([NH:1][C:2]2[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=2[C:4]([NH:6][CH2:7][C:8]#[CH:9])=[O:5])[C:29]([Cl:33])=[CH:28][N:27]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 27644242-Amino-N-(prop-2-yn-1-yl)benzamide

생성물 1

HCID 866340252-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide수율 4%

실험 절차

2-Amino-N-prop-2-ynyl-benzamide (4.20 g, 24.1 mmol) was dissolved in N,N-dimethylformamide (100 mL, 1.290 mol) and potassium carbonate (5.00 g, 36.2 mmol) was added. 2,4,5-Trichloro-pyrimidine (3.32 mL, 28.9 mmol) was added and the reaction was stirred for 48 hours. The reaction was concentrated under reduced pressure and the residue was taken up in DCM (300 mL) and washed with water (300 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-50% EtOAc/hex as the eluting solvent to obtain 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-prop-2-ynyl-benzamide as a pale yellow solid (298 mg, 4%). m.p.=188-191° C.; LCMS (m/e) 321 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 11.53 (s, 1H), 8.76 (d, 1H, J=8.5 Hz), 8.25 (s, 1H), 7.66-7.53 (m, 2H), 7.23-7.14 (m, 1H), 6.39 (bs, 1H), 4.34-4.25 (m, 2H), 2.34 (t, 1H, J=2.5 Hz).

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with water (300 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-cfde8d8962e64d438411bf93a095cf52
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552186B2

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