Dimethylamine → 6-dimethylamino-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 2400106

반응식

HRID 2400106 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([CH2:14][C:15]#[CH:16])[C:4](=[O:17])[C:3]=1[CH3:18].[CH3:19][NH:20][CH3:21]>O1CCCC1.CCOCC>[CH3:19][N:20]([CH3:21])[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([CH2:14][C:15]#[CH:16])[C:4](=[O:17])[C:3]=1[CH3:18]

참가 물질

5

반응물 2

HCID 674DimethylamineHCID 196907006-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

생성물 1

HCID 196906956-dimethylamino-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To an ice cooled solution of 1.5 g (3.8 mmol) 6-chloro-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 4 mL of tetrahydrofuran, was added 22 mL (99 mmol) of 4.5M dimethylamine in ether portionwise (2-4 mL) over a period of 7 days. The reaction mixture was allowed to warm and stir at room temperature after each addition. The progress of the reaction was followed by gas chromatography and proceeded to 80% completion. The solvent was removed in vacuo and the residue was taken up in ether and washed twice with water. The organic layer was dried over MgSO4 and concentrated to yield 1.15 g crude solid product. Flash column chromatography on silica gel (gradient elution 25-30% ethyl acetate-hexane) afforded pure 6-dimethylamino-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (compound 23), as a white solid. 1H-NMR (CDCl3)δ2.2 (3H, s); 2.35 (1H, t); 3.5 (6H, s); 4.6 (2H, d); 7.65 (3H, m); 7.75 (2H, m).

후처리

  1. temperatureto warm
  2. additionafter each addition
  3. customThe solvent was removed in vacuo
  4. washwashed twice with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customto yield 1.15 g crude solid product

출처 및 근거

ORD 기록
ord-19f4b21d97164a299e3afaf31d2e131a
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05453414

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