Triethylamine → Racemic 3-(10-(4-chlorothiazol-2-yl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

HRID 2201215Notes

Reaction equation

HRID 2201215 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[Cl:16][C:17]1[N:18]=[C:19]([CH:22](O)[CH2:23][CH2:24][CH2:25][N:26]2[C:34]([C:35]3[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=3)[C:38]#[N:39])=[C:33]3[C:28]([N:29]([CH3:46])[C:30](=[O:45])[N:31]([CH3:44])[C:32]3=[O:43])=[CH:27]2)[S:20][CH:21]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:16][C:17]1[N:18]=[C:19]([CH:22]2[C:27]3[N:26]([C:34]([C:35]4[CH:36]=[C:37]([CH:40]=[CH:41][CH:42]=4)[C:38]#[N:39])=[C:33]4[C:32](=[O:43])[N:31]([CH3:44])[C:30](=[O:45])[N:29]([CH3:46])[C:28]4=3)[CH2:25][CH2:24][CH2:23]2)[S:20][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 867234543-(6-(4-(4-Chlorothiazol-2-yl)-4-hydroxybutyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Product 1

HCID 77106222Racemic 3-(10-(4-chlorothiazol-2-yl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Trifluoromethanesulfonic anhydride (3.95 ml, 23.41 mmol) was added dropwise to a solution of 3-(6-(4-(4-chlorothiazol-2-yl)-4-hydroxybutyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (5 g, 10.64 mmol) and triethylamine (3.56 ml, 25.5 mmol) in DCM (213 mL) at −78° C. The mixture was stirred for 1 min at −78° C. The reaction was quenched with saturated aqueous NaHCO3(aq) (100 mL) and extracted with DCM (3×100 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under reduced pressure to afford crude racemic 3-(10-(4-chlorothiazol-2-yl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3(aq) (100 mL)
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2f3d8dead5f64eec9296cccbd7bb3a8c
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

Loading…