Hydrochloric Acid → HCID 178490864, compound

HRID 2410016Notes

Reaction equation

HRID 2410016 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:17]([OH:18])=[C:16]([C:19](OCC)=[O:20])[C:15](=[O:24])[N:14]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]1=[O:32].C1(CNC([CH:43](C(OCC)=O)[C:44]([O:46]CC)=[O:45])=O)C=CC=CC=1.[H-].[Na+].COC1C=C(OC)C=CC=1C[N:61]=C=O.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]1[C:17]([OH:18])=[C:16]([C:19]([NH:61][CH2:43][C:44]([OH:46])=[O:45])=[O:20])[C:15](=[O:24])[N:14]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:13]1=[O:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 112525271-(Isocyanatomethyl)-2,4-dimethoxybenzeneHCID 25241833HCID 25241833, compoundHCID 178470075HCID 178470075, compound

Product 1

HCID 178490864HCID 178490864, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-{[2,4-bis(methyloxy)phenyl]methyl}-6-hydroxy-2,4-dioxo-3-(phenylmethyl)-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate. Diethyl {[(phenylmethyl)amino]carbonyl}propanedioate (820 mg, 2.8 mmoles) was added to a suspension of sodium hydride (60% suspension in mineral oil, 280 mg, 7.0 mmoles) in dry tetrahydrofuran (50 mL) and stirred for 10 minutes under argon. 2,4-dimethoxybenzyl isocyanate (1.0 mL, 6.0 mmoles) was added and the mixture heated under reflux for 3 hours, cooled, acidified with 1 molar hydrochloric acid and extracted with ethyl acetate. Flash chromatography (30% methanol in dichloromethane) afforded the title compound (480 mg, 39%) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (t, J=6.69 Hz, 3 H) 3.71 (s, 3 H) 3.78 (s, 3 H) 4.09 (q, J=5.05 Hz, 1 H) 4.81 (s, 2 H) 4.92 (s, 2 H) 6.40-6.59 (m, 3 H) 6.62-7.26 (m, 5 H).

Workup

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

Sources & evidence

ORD record
ord-cc2194cd3d2c4b9c9400519226c7c854
Source dataset
uspto-grants-2014_08
Patent number
US08815884B2

Reaction notes

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