Ammonium Chloride → 2-Methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

HRID 1289220Notes

Reaction equation

HRID 1289220 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1[NH:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][C:12]3[CH2:21][CH2:20][CH2:19][C:13]=3[CH:14]=2)[N:9]=1.[C:22]([O:28][CH2:29]Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C.O>[CH3:7][C:8]1[N:17]([CH2:29][O:28][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:16](=[O:18])[C:15]2[C:10](=[CH:11][C:12]3[CH2:21][CH2:20][CH2:19][C:13]=3[CH:14]=2)[N:9]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 87885Chloromethyl pivalateHCID 23665647Potassium tert-butoxideHCID 1355040542-Methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

Product 1

HCID 108527582-Methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (64 g) was added portionwise during 15 minutes to a stirred solution of 2-methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one (89 g) in DMSO (700 ml). The mixture was stirred at ambient temperature for 30 minutes. Chloromethyl pivaloate (131 g) was added dropwise during 30 minutes. The mixture was stirred at ambient temperature for 24 hours. The mixture was poured into a mixture of ammonium chloride (500 g) and a mixture (3 L) of ice and water. Ethyl acetate (2 L) was added and the mixture was filtered. The organic layer was dried (MgSO4) and evaporated. The residue was triturated under diethyl ether (500 ml). The mixture was cooled to 0° C. for 2 hours. The solid was isolated, washed with diethyl ether and dried. There was thus obtained 2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one (72.4 g), m.p. 128° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 24 hours
  2. filtrationthe mixture was filtered
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated
  5. customThe residue was triturated under diethyl ether (500 ml)
  6. temperatureThe mixture was cooled to 0° C. for 2 hours
  7. customThe solid was isolated
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-2ca552bb2edf46639c48170bc8ff3989
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

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