Triethylamine → 9-(4-Chlorothiazol-2-yl)-1,3-dimethyl-5-phenyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

HRID 2201221Notes

Reaction equation

HRID 2201221 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:7](O)[CH2:8][CH2:9][N:10]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:17]3[C:12]([N:13]([CH3:28])[C:14](=[O:27])[N:15]([CH3:26])[C:16]3=[O:25])=[CH:11]2)[S:5][CH:6]=1.C(N(CC)CC)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([CH:7]2[C:11]3[N:10]([C:18]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[C:17]4[C:16](=[O:25])[N:15]([CH3:26])[C:14](=[O:27])[N:13]([CH3:28])[C:12]4=3)[CH2:9][CH2:8]2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 67749Trifluoromethanesulfonic anhydrideHCID 867234586-(3-(4-Chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 771068369-(4-Chlorothiazol-2-yl)-1,3-dimethyl-5-phenyl-8,9-dihydro-1H-pyrimido[4,5-a]pyrrolizine-2,4(3H,7H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluromethanesulfonic anhydride (0.576 mL, 3.41 mmol) in DCM (3 mL) was added slowly to a solution of 6-(3-(4-chlorothiazol-2-yl)-3-hydroxypropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (490 mg, 1.137 mmol) and triethylamine (0.792 mL, 5.69 mmol) in DCM (40 mL) at 0° C. Further portions of triethylamine (0.792 mL, 5.69 mmol) and trifluoromethanesulfonic anhydride (0.576 mL, 3.41 mmol) were added to allow the reaction to run to completion. The reaction was quenched with saturated NaHCO3(aq) and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under vacuum. Purification by mass-directed HPLC under the following conditions afforded the title compound.

Workup

  1. customthe reaction
  2. customThe reaction was quenched with saturated NaHCO3(aq)
  3. extractionextracted with DCM
  4. customevaporated under vacuum
  5. customPurification by mass-directed HPLC under the following conditions

Sources & evidence

ORD record
ord-c6018f784b86418c93e327f0cc19d092
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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