HCID 24957971, compound → HCID 24958345, compound

HRID 1258424Notes

Reaction equation

HRID 1258424 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:18][C:12]3[NH:13][C:14](=[O:17])[N:15]=[CH:16][C:11]=3[C:10]=2[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[CH:5][C:4]=1[O:31]COCCOC>C1COCC1.CO.Cl.CCOC(C)=O>[OH:31][C:4]1[CH:5]=[C:6]([C:9]2[O:18][C:12]3[NH:13][C:14](=[O:17])[N:15]=[CH:16][C:11]=3[C:10]=2[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 1

HCID 24957971HCID 24957971, compound

Product 1

HCID 24958345HCID 24958345, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[4-Methoxy-3-(2-methoxy-ethoxymethoxy)-phenyl]-5-(3,4,5-trimethoxyphenyl)-1H-furo[2,3-d]pyrimidin-2-one (Example 6) (102 mg, 0.2 mmol) was dissolved in mixture of THF (2 ml) and MeOH (2 ml) and 0.2 ml of concentrated HCl was added slowly with stirring. The reaction mixture was stirred for overnight with slow evaporation of solvents. The residue was dissolved in EtOAc (50 ml) and washed with water (5 ml). The organic layer was concentrated and purified by silica gel column chromatography using increasing gradient of EtOAc in CH2Cl2 and finally with 5% MeOH in 1:1 mixture of EtOAc and CH2Cl2. Yield (42%); 1H NMR (300 MHz, DMSO-d6) δ: 3.69 (s, 9H, 3×OMe), 3.75 (s, 3H, OMe), 6.71 (s, 2H), 6.92-7.11 (m, 3H), 8.15 (s, 1H).

Workup

  1. additionwas added slowly
  2. stirringThe reaction mixture was stirred for overnight with slow evaporation of solvents
  3. washwashed with water (5 ml)
  4. concentrationThe organic layer was concentrated
  5. custompurified by silica gel column chromatography
  6. temperatureusing increasing gradient of EtOAc in CH2Cl2
  7. additionfinally with 5% MeOH in 1:1 mixture of EtOAc and CH2Cl2
  8. customYield (42%)

Sources & evidence

ORD record
ord-133a1200e9cb42628e76ab8d1a537bcd
Source dataset
uspto-grants-2013_06
Patent number
US08466163B2

Reaction notes

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