5,6-Dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one → 4-chloro-5,6-dimethyl-N-(pyridin-2-ylmethyl)pyrimidin-2-amine

HRID 63122

반응식

HRID 63122 반응식
[CH3:1][C:2]1[C:3](=O)[NH:4][C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[N:6][C:7]=1[CH3:8].O(Cl)[Cl:19].[P+5]>CN(C)C=O>[Cl:19][C:3]1[C:2]([CH3:1])=[C:7]([CH3:8])[N:6]=[C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:4]=1

참가 물질

4

반응물 2

HCID 1363714865,6-Dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-oneHCID 178479711HCID 178479711, 화합물

생성물 1

HCID 832906664-chloro-5,6-dimethyl-N-(pyridin-2-ylmethyl)pyrimidin-2-amine수율 74%

시약·촉매·용매 1

HCID 6228Dimethylformamide촉매

실험 절차

A solution of 5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one (7.0 g, 32.6 mmol, Step B) in phosphorus (V) oxychloride (30 mL) with addition of 1 drop of dimethylformamide was refluxed overnight under nitrogen. Then excess phosphorus (V) oxychloride was removed under reduced pressure. Toluene (30 mL) was added, and the reaction mixture was evaporated under reduced pressure. The residue was diluted with 5% aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (2×200 mL). The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography eluted with hexane/ethyl acetate (2:1). The titled compound 6.1 g (74%) was obtained as a light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.10 (s, 3H), 2.39 (s, 3H), 4.54 (s, 2H), 7.20-7.30 (m, 2H), 7.68-7.76 (m, 2H), 7.76 (bs, 1H).

후처리

  1. temperaturewas refluxed overnight under nitrogen
  2. customThen excess phosphorus (V) oxychloride was removed under reduced pressure
  3. additionToluene (30 mL) was added
  4. customthe reaction mixture was evaporated under reduced pressure
  5. additionThe residue was diluted with 5% aqueous sodium bicarbonate (100 mL)
  6. extractionextracted with ethyl acetate (2×200 mL)
  7. customThe solvent was evaporated under reduced pressure
  8. washeluted with hexane/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-b29a66f33a4d443984c44429506d74d6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447051B2

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