Water → Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-7,8-dihydroquinazoline-6-carboxylate

HRID 1766082Notes

Reaction equation

HRID 1766082 reaction equation
[C:1]([C:3]1[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=[N:5][C:6]([S:22][CH3:23])=[N:7][C:8]=1[CH2:9][CH2:10][CH:11](C(OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:2].[Sn](Cl)(Cl)(Cl)Cl.O.CCOC(C)=O>C(Cl)Cl>[NH2:2][C:1]1[C:3]2[C:4]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)=[N:5][C:6]([S:22][CH3:23])=[N:7][C:8]=2[CH2:9][CH2:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24287Tin tetrachlorideHCID 211090855-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-(1,1-bis(ethoxycarbonyl)prop-3-yl)pyrimidine

Product 1

HCID 21109093Ethyl 5-amino-2-methylthio-4-(3-methoxyphenyl)-7,8-dihydroquinazoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-(1,1-bis(ethoxycarbonyl)prop-3-yl)pyrimidine (example 25b, 81 mg) was dissolved in dry CH2Cl2 (1 ml). A 1M solution of tin(IV) chloride in CH2Cl2 (1 ml) was added dropwise and the mixture was stirred at room temperature for 1 h. H2O (10 ml) and EtOAc (10 ml) were then added to the reaction mixture. The organic layer was washed with H2O (10 ml) and sat. aq. NaCl (10 ml), dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/EtOAc=1/0 to 3/2 (v/v) as eluent.

Workup

  1. washThe organic layer was washed with H2O (10 ml) and sat. aq. NaCl (10 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe title compound was purified by chromatography on silica gel with hept/EtOAc=1/0 to 3/2 (v/v) as eluent

Sources & evidence

ORD record
ord-215c73b9b13c401c9b6cca7aaf8b09b9
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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