Triethylamine → HCID 18697989, compound

HRID 2289546Notes

Reaction equation

Cl.[CH3:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][N:4]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:28](OC2C=CC([N+]([O-])=O)=CC=2)=[O:29])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][N:25]([C:28]([N:12]2[CH2:11][CH2:10][N:9]([C:7]3[CH:6]=[CH:5][N:4]=[C:3]([CH3:2])[N:8]=3)[CH2:14][CH2:13]2)=[O:29])[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 110 °C

Procedure

2-Methyl-4-(1-piperazinyl)pyrimidine hydrochloride (18.80 g) and 1-(tert-butoxycarbonyl)-4-(4-nitrophenyloxycarbonyl) piperazine (25 g) were stirred in dry DMF (250 ml) and triethylamine (40 ml) under argon. The reaction mixture was stirred at 110° C. for 5 hours and then allowed to cool overnight. The solid was collected by filtration, washed with DMF and isohexane. The solid was purified by chromatography on silica gel using a gradient of dichloromethane to 5% methanol in dichloromethane as eluent to give 1-(tert-butoxycarbonyl)-4-(1-(2-methylpyrimidin-4-yl)piperazin-4-ylcarbonyl)piperazine as a pale solid (19.92g); NMR (CDCl3): 8.15 (m, 1H), 6.35 (m, 1H), 3.7 (m, 4H), 3.45 (m, 4H), 3.35 (m, 4H), 3.3 (m, 4H), 2.5 (s, 3H), 1.45 (s, 9H).

Workup

temperatureto cool overnight
filtrationThe solid was collected by filtration
washwashed with DMF and isohexane
customThe solid was purified by chromatography on silica gel using a gradient of dichloromethane to 5% methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-c6eaa793788c43cfa53e4a37841ec860
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093718

Reaction notes

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