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

HRID 1463242

反応式

HRID 1463242 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 (6 H, s); 4.6 (2H, d); 7.65 (3H, m); 7.75 (2H, m).

後処理

  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

出典と根拠

ORDレコード
ord-d4e0241896864adf838a441aac17a3cf
出典データセット
uspto-grants-1994_04
特許番号
US05300477

関連ノート

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