Acetonitrile → N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine

HRID 474262노트

반응식

HRID 474262 반응식
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[CH:19]([N:22]([CH:25](C)C)CC)(C)[CH3:20].C(#[N:30])C>>[Cl:1][C:2]1[N:3]=[C:4]([NH:30][CH2:20][CH2:19][NH:22][CH3:25])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

참가 물질

4

반응물 3

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 580754242,4-Dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[D]pyrimidine

생성물 1

HCID 86668110N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine수율 70.6%

실험 절차

To a solution of 2,4-dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H cyclopenta[d]pyrimidine (2.0 g, 7.06 mmol) in acetonitrile (50 mL) was added diisopropylethylamine (1.369 g, 10.60 mmol) followed by N-1-methylethane-1,2-diamine (0.628 g, 8.48 mmol) at room temperature. The reaction mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and the residue was taken in dichloromethane (10 mL) and silica (2 g). The resultant slurry of the compound on silica was subjected to flash chromatography using a Teledyne Isco instrument (12 g RediSep silica column, 10% methanol in chloroform) to get N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine (1.6 g, 70.6%) as a light brown solid. LC-MS (M+H)+=321.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.13 (2H, br s), 7.22-7.11 (4H, m), 4.21-4.17 (1H, t, J=8.0 Hz), 3.82-3.79 (2H, m), 3.27 (3H, s), 3.19-3.04 (4H, m), 2.55-2.54 (1H, m), 1.99-1.98 (1H, m).

후처리

  1. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-087692eff4cd4c39a4346fb4f6758ced
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637523B2

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