Ethyl isocyanate → HCID 58138376, compound

HRID 1038954Notes

Reaction equation

HRID 1038954 reaction equation
[F:1][C:2]1[C:3]([NH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[O:11])=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH2:22]([N:24]=[C:25]=[O:26])[CH3:23]>C1COCC1>[CH2:22]([NH:24][C:25]([N:6]1[CH:7]=[C:2]([F:1])[C:3]([NH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[O:11])=[N:4][C:5]1=[O:8])=[O:26])[CH3:23]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 178489515HCID 178489515, compound

Product 1

HCID 58138376HCID 58138376, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)-3-(2-methoxybenzyl)urea (as prepared in U.S. Patent Appl. Publ. 2010022538; 0.25 g, 0.855 mmol) in dry THF (5 mL) was added ethyl isocyanate (0.074 mL, 0.941 mmol), and the mixture was stirred at room temperature for 3 h. The solvent was removed in vacuo, and the solid residue was suspended in Et2O (10 mL). The suspension was suction filtered and washed with Et2O (2×10 mL). The resulting solid was dried in vacuo to yield N-ethyl-5-fluoro-4-(3-(2-methoxybenzyl)ureido)-2-oxopyrimidine-1(2H)-carboxamide (0.150 g, 48%) as a white solid: mp 248-250° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.56 (s, 1H), 9.92 (s, 1H), 9.68 (s, 1H), 8.55 (d, J=6.6 Hz, 1H), 7.33-7.20 (m, 2H), 7.02 (d, J=7.9 Hz, 1H), 6.91 (dd, J=7.9, 6.9 Hz, 1H), 4.41 (d, J=6.0 Hz, 2H), 3.88 (s, 3H), 3.38-3.24 (m, 2H), 1.14 (t, J=7.2 Hz, 3H). ESIMS m/z 362 ([M−H]−).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationfiltered
  3. washwashed with Et2O (2×10 mL)
  4. customThe resulting solid was dried in vacuo

Sources & evidence

ORD record
ord-496a4225a90f41e48baa50285a48fad1
Source dataset
uspto-grants-2013_10
Patent number
US08552020B2

Reaction notes

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