HCID 178472250, compound → HCID 178450469, compound

HRID 1365740Notes

Reaction equation

HRID 1365740 reaction equation
C(OC(=O)C([O:12][NH:13][C:14](=[NH:23])[C:15]([CH3:22])([CH3:21])[CH2:16][O:17][CH2:18][CH2:19][Cl:20])=CC(OCC)=O)C.ClCCOCC(C1NC(=O)C(O)=C(C(OCC)=O)N=1)(C)C>CC1C=CC(C)=CC=1C>[Cl:20][CH2:19][CH2:18][O:17][CH2:16][C:15]([CH3:22])([CH3:21])[C:14]([NH:13][OH:12])=[NH:23]

Participants

3

Reactant 1

HCID 178472250HCID 178472250, compound

Product 1

HCID 178450469HCID 178450469, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 72471,2,4-TrimethylbenzeneSolvent

Conditions

Temperature
157.5 °C

Procedure

Ethyl 2-(1-(2-chloroethoxy)-2-methylpropan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate Diethyl 2-(3-(2-chloroethoxy)-2,2-dimethylpropanimidamidooxy)but-2-enedioate was dissolved in 150 mL 1,2,4-trimethylbenzene and heated at 155-160° C. for 2.5 hrs with stirring under N2. The solvent was evaporated at reduced pressure and the residue was dissolved in EtOAc and extracted 2× with dil NaHCO3. The aqueous extracts were acidified with HCl and extracted with CH2Cl2. After drying (MgSO4), filtration and concentration provided the title compound (1.9 g, 43%) as a white solid. 1H NMR (300 MHz, CDCl3) δ: 1.31 (s, 6H), 1.41 (t, J=7.1 Hz, 3H), 3.54 (s, 2H), 3.63-3.72 (m, 2H), 3.75-3.83 (m, 2H), 4.42 (q, J=7.3 Hz, 2H). LC/MS (M+H): 319.

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionextracted 2× with dil NaHCO3
  4. extractionextracted with CH2Cl2
  5. customAfter drying
  6. filtration(MgSO4), filtration and concentration

Sources & evidence

ORD record
ord-32fc3a90593b411096299b920e766e52
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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