Morpholine → HCID 69661871, compound
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].N1CC[O:29]CC1>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8](=[O:29])[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
Procedure
5-Benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.215 g, 0.58 mmol) was reacted with morpholine as described in the preparation of compound 1J. Chromatography on silica gel (elution toluene-ethyl acetate 8:2 to 6:4) gave first 0.050 g (30% yield) of 5-benzyloxy-1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid ethyl ester as white crystals; mp 184–187° C. (ethyl acetate). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.34 (3H, t, J=7.1 Hz, CH3), 3.40 (3H, s, NCH3), 4.39 (2H, q, J=7.1 Hz, OCH2), 5.16 (3H, s, OCH2), 7.35–7.5 (5H, m, aromatics), 8.12 (1H, broad s, NH). Anal. Calcd for C15H16N2O5: C, 59.20; H, 5.30; N, 9.20. Found: C, 59.20; H, 5.08, N 9.19 . The end fractions then gave 0.102 g (47% yield) of the title ester as a white syrup. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.29 (3H, t, J=7.1 Hz, CH3), 3.20 (4H, m, NCH2), 3.53 (3H, s, NCH3), 3.82 (4H, m, OCH2), 4.32 (2H, q, J=7.1 Hz, OCH2), 5.17 (2H, s, OCH2), 7.29–7.49 (5H, m, aromatics). HRMS (FAB POS) calculated for C19H24N3O5 [M+H+]: 374.171596. found: 374.1709485
Sources & evidence
- ORD record
- ord-ff98eb229e054760b27114917f72f306
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135467B2
Reaction notes
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