Benzyl (2-(4-((4-fluorobenzyl)carbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)carbamate synthesis

7synthesis methods

Product Name:Benzyl (2-(4-((4-fluorobenzyl)carbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)carbamate
CAS Number:519028-33-2
Molecular formula:C23H23FN4O5
Molecular Weight:454.45

519032-08-7 Synthesis

4-PYRIMIDINECARBOXYLIC ACID, 1,6-DIHYDRO-5-HYDROXY-2-[1-METHYL-1-[[(PHENYLMETHOXY)CARBONYL]AMINO]ETHYL]-6-OXO-, METHYL ESTER

519032-08-7
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140-75-0 Synthesis

140-75-0
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Benzyl (2-(4-((4-fluorobenzyl)carbamoyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidin-2-yl)propan-2-yl)carbamate

519028-33-2
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Yield:519028-33-2 98%

Reaction Conditions:

with triethylamine in methanol at 65 - 68; for 7 h;

Steps:

1.1

A round bottom flask was charged with methyl 2-(l-{[(benzyloxy)carbonyl]amino}-l-methylethyl)-5,6-dihydroxypyrimidine-4-carboxylate (Compound I; 1 eq.) and methanol (-1.6 mL per gram of Compound 1). The slurry was warmed to 55°C, after which triethylamine (1.2 eqs.) was added in one portion. The solution was then warmed to 65°C and 4-fluorobenzylamine (1.2 eqs) was added at 65-68°C. The mixture was then aged at reflux for 7 hours. The solution was cooled to 55⁰C₅ and acetic acid (2 eqs.) was added in one portion. Water was added followed by seed crystals of 2. (Note: Crystallization would occur without seed, but seeding provides a more reliable method of crystal growth.) The resultant slurry was aged at 6O⁰C with the addition of more water during the ageing. The slurry was then cooled to 2O⁰C₅ filtered, washed with 1 : 1 methanol:water, and dried in a nitrogen stream to give compound 2 (96 wt.% purity by HPLC assay, 1.75 wt.% water by Karl Fisher titration), 98% overall yield (corrected for purity). Compound 2: lH NMR (600.13 MHz, CDCI3) δ 12.37 (br s, 2H), 7.95 (br t, J~6 Hz, IH), 735-7.31 (m, 2H)₅7.25-7.19 ( br m, 5H), 7.08-7.04 (m, 2H), 6.49 (s, IH)₅ 4.96 (s, 2H)₅ 4.58 (d, 3=6.0 Hz, 2H)₅ 1.64 (s, 6H).13C NMR (150.92 MHz, CDCI3) δ 168.5, 162.6 (d, JcF=246.6 Hz), 160.O₅ 155.3₅ 154.1, 147.9, 136.5, 133.1 (d, JCF=3-1 Hz), 129.7 (d, JCF^7.9 Hz), 128.6, 128.1, 127.9, 127.1, 116.0 (d₅ JCF=22.0 Hz), 66.8, 55.5, 42.7, 26.7.