1-(1,1-Dimethylethyl) 2-methyl 1,2-piperazinedicarboxylate → HCID 71240780, compound

HRID 1774613Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH3:16][O:17][C:18]([CH:20]1[CH2:25][NH:24][CH2:23][CH2:22][N:21]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:19]>C(O)(C)(C)C>[CH3:16][O:17][C:18]([CH:20]1[CH2:25][N:24]([C:2]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=3)[N:5]=[CH:4][N:3]=2)[CH2:23][CH2:22][N:21]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:19]

Participants

Conditions

Temperature: 150 °C

Procedure

4-Chloro-6-(3,4-dichloro-phenyl)-pyrimidine (0.11 g, 0.4 mmol) was added in one portion to a suspension of piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.21 g, 0.85 mmol) and in tert-butanol (2 ml) in a microwave reactor tube. The tube was sealed and heated to 150° C. in a microwave for 40 minutes at a pressure of 250 psi. After this time the reaction mixture was cooled to room temperature and the solvent was removed. The resulting residue was purified by flash column chromatography (elution: 20% EtOAc, 80% Heptane) to give the title compound (0.36 g, 75% yield) as a colourless oil. δH (500 MHz, DMSO) 8.59 (s, 1H) 8.43 (d, J=2.05 Hz, 1H) 8.17 (dd, J=8.51, 2.05 Hz, 1H) 7.74-7.81 (m, 1H) 7.42 (d, J=7.88 Hz, 1H) 4.88-5.09 (m, 1H) 4.60-4.76 (m, 1H) 4.24-4.46 (m, 1H) 3.76-3.88 (m, 1H) 3.56 (d, J=13.08 Hz, 3H) 3.38-3.51 (m, 1H) 3.10-3.28 (m, 2H) 1.31-1.47 (m, 9H). Tr=3.71 min m/z (ES+) (M+H+) 283, 285.

Workup

customThe tube was sealed
temperatureAfter this time the reaction mixture was cooled to room temperature
customthe solvent was removed
customThe resulting residue was purified by flash column chromatography (elution: 20% EtOAc, 80% Heptane)

Sources & evidence

ORD record: ord-55c5a54cc3d545fdb62f395f53d42810
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260422B2

Reaction notes

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