1-(2-Hydroxyethyl)piperazine → HCID 58739055, compound

HRID 720295Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](S(C)(=O)=O)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].[OH:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:32]2[CH2:33][CH2:34][N:29]([CH2:28][CH2:27][OH:26])[CH2:30][CH2:31]2)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 5-Benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.10 g, 0.27 mmol) dissolved in THF (1 mL) was added 1-(2-hydroxyethyl)piperazine (0.05 mL, 0.41 mmol). The resulting mixture was stirred at 70° C. for 3 hours. The mixture was concentrated and the resulting residue was purified by flash chromatography, eluting with 2% MeOH/CH2Cl2 to yield the title compound as a pale yellow oil (0.0423 g, 38% yield). 1H NMR (500 MHz, CDCl3) δ: 7.45 (2H, d, J=7.0 Hz), 7.35–7.27 (3H, m), 5.14 (2H, s), 4.30 (2H, q, J=7.1 Hz), 3.63 (2H, t, J=5.3 Hz), 3.49 (3H, s), 3.21 (4H, t, J=4.7 Hz), 2.63 (4H, bs), 2.59 (2H, t, J=5.3 Hz), 1.27 (3H, t, J=7.2 Hz). HRMS (M+H) calcd for C21H29N4O5: 417.21381. found: 417.2147.

Workup

concentrationThe mixture was concentrated
customthe resulting residue was purified by flash chromatography
washeluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record: ord-631b1736ebfc4168badaca3fcb3da5dc
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135467B2

Reaction notes

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