Chloroacetonitrile → HCID 86673651, compound

HRID 1476581Notes

Reaction equation

HRID 1476581 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:5]=2[C:4](=[O:17])[N:3]1[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.Cl[CH2:32][C:33]#[N:34].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:33]([CH2:32][N:7]1[C:6]2[CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:10][C:5]=2[C:4](=[O:17])[N:3]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[C:2]1=[O:1])#[N:34]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 67257815tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate

Product 1

HCID 86673651HCID 86673651, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 4-(2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl)piperidine-1-carboxylate (5 g; compound B50) and chloroacetonitrile (883 mg) in DMF (45 ml) is added potassium carbonate (1.62 g). The mixture is stirred for 1 h at 100° C. and then poured into ice-cold water. The resulting precipitate is filtered off, washed with water and dried under reduced pressure to give tert-butyl 4-[1-(cyanomethyl)-2,4-dioxo-6-phenyl-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate (compound B14a) as a solid, which is used without further purification for the next step.

Workup

  1. additionpoured into ice-cold water
  2. filtrationThe resulting precipitate is filtered off
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-253b5cc9bd5b4b54873223a0531b716e
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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