Water → HCID 68675425, compound

HRID 1993309Notes

Reaction equation

HRID 1993309 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=[O:20])[NH:10][C:11]3[C:16]=2[CH:15]=[C:14]2[CH:17]=[CH:18][CH:19]=[C:13]2[CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:28][CH3:29].O>CN(C=O)C>[CH2:28]([O:20][C:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[CH2:15][C:14]3=[CH:17][CH:18]=[CH:19][C:13]3=[CH:12][C:11]=2[N:10]=1)[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 23505643HCID 23505643, compound

Product 1

HCID 68675425HCID 68675425, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-phenylcyclopenta[g]quinazolin-2(1H)-one (120 mg, 0.46 mmol) and K2CO3 (76 mg, 0.55 mmol) in 4 mL of DMF was added iodoethane (44 μL, 0.55 mmol) and stirred at rt overnight. Water was then added and the resulting suspension extracted with 2×20 mL of EtOAc. The extract was washed with water twice and brine, then dried over MgSO4 and concentrated in vacuo. The crude solid was then subjected to flash column chromatography eluting with acetone/hexane to give the title compound 2-ethoxy-4-phenyl-cyclopenta[g]quinazoline (25 mg, 19%) followed by the title compound 1-ethyl-4-phenylcyclopenta[g]quinazolin-2(1H)-one (66 mg, 50%). 1H NMR (CDCl3): 7.7 (d, 2H), 7.63 (s, 1H), 7.53 (m, 3H), 7.29 (s, 1H), 4.38 (q, 2H), 3.09 (t, 2H), 2.93 (t, 2H), 2.16 (p, 2H), 1.45 (t, 3H).

Workup

  1. extractionthe resulting suspension extracted with 2×20 mL of EtOAc
  2. washThe extract was washed with water twice
  3. dry with materialbrine, then dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washeluting with acetone/hexane

Sources & evidence

ORD record
ord-cf8337bd6a2c41809aebbdb817ae657f
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

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