1-Naphthaldehyde → 1-Naphthaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone

HRID 1181806

반응식

HRID 1181806 반응식
[NH:1]([C:3]1[NH:8][C:7](=[O:9])[N:6]([CH3:10])[C:5](=[O:11])[CH:4]=1)[NH2:2].[C:12]1([CH:22]=O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH3:10][N:6]1[C:5](=[O:11])[CH:4]=[C:3]([NH:1][N:2]=[CH:22][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[NH:8][C:7]1=[O:9]

참가 물질

4

반응물 2

HCID 61951-NaphthaldehydeHCID 113786296-hydrazino-3-methylpyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 698455281-Naphthaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 84 mg (0.54 mmol) 6-hydrazino-3-methylpyrimidine-2,4(1H,3H)-dione and 84 mg (0.54 mmol) 1-naphthaldehyde in 3 mL DMF was heated to 70° C. for 30 min before cooling to room temperature affording a solution of 1-naphthaldehyde (1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)hydrazone. Isonicotinaldehyde (110 mg, 1.0 mmol) and piperidine (50 μL, 0.6 mmol) were added, and the mixture was heated at 70° C. for 20 h. 1,1,1-trifluoro-2-iodoethane (130 μL, 1.3 mmol) and DBU (200 μL, 1.3 mmol) were added, and the mixture was heated at 90° C. for 20 h. Solvent was removed and the residue was purified by preparative reverse phase HPLC (30%-60% gradient of CH3CN-water with 0.1% TFA) to afford the title compound as the trifluoroacetate salt.

출처 및 근거

ORD 기록
ord-dbc3a48b624143f0b49838a2aecaa803
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285558B2

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