Hydrochloric Acid → HCID 178525915, compound

HRID 2410015Notes

Reaction equation

HRID 2410015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([OH:14])=[C:12]([C:15](OCC)=[O:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:9]2=[O:28])=[CH:4][CH:3]=1.C1(CNC([CH:39](C(OCC)=O)[C:40]([O:42]CC)=[O:41])=O)C=CC=CC=1.[H-].[Na+].ClC1C=CC([N:59]=C=O)=CC=1.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13]([OH:14])=[C:12]([C:15]([NH:59][CH2:39][C:40]([OH:42])=[O:41])=[O:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:9]2=[O:28])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 76934-Chlorophenyl IsocyanateHCID 24758Sodium hydrideHCID 25241833HCID 25241833, compoundHCID 178470054HCID 178470054, compound

Product 1

HCID 178525915HCID 178525915, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(4-chlorophenyl)-6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate. Diethyl {[(phenylmethyl)amino]carbonyl}propanedioate (293 mg, 1.0 mmoles) was added to a suspension of sodium hydride (60% suspension in mineral oil, 100 mg, 2.5 mmoles) in dry tetrahydrofuran (50 mL) and stirred for 10 minutes under argon. 4-Chlorophenyl isocyanate was added and the mixture was heated under reflux for 2 hours, cooled, acidified with 1 molar hydrochloric acid and extracted with ethyl acetate. Flash chromatography (hexane-ethyl acetate) afforded the title compound (225 mg, 56%) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06 (t, J=7.07 Hz, 3 H) 3.45 (q, J=7.07 Hz, 2 H) 5.00 (s, 2 H) 7.25-7.28 (m, 1 H) 7.30-7.37 (m, 6 H) 7.53 (d, J=8.59 Hz, 2 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-599f795d4f04447bbb39023971927893
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

Loading…