Potassium Carbonate → tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

HRID 1476626Notes

Reaction equation

HRID 1476626 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]4)[C:12](=[O:31])[NH:11][C:10]=3[CH:9]=2)=[C:4]([O:32][CH3:33])[CH:3]=1.Cl[CH2:35][C:36]1[O:40][N:39]=[C:38]([CH2:41][O:42][CH3:43])[N:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:19]4)[C:12](=[O:31])[N:11]([CH2:35][C:36]4[O:40][N:39]=[C:38]([CH2:41][O:42][CH3:43])[N:37]=4)[C:10]=3[CH:9]=2)=[C:4]([O:32][CH3:33])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 252192435-(Chloromethyl)-3-(methoxymethyl)-1,2,4-oxadiazoleHCID 67259586tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Product 1

HCID 67258937tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate (1.0 g, compound B63) and 5-(chloromethyl)-3-(methoxymethyl)-1,2,4-oxadiazole (342 mg) in dry DMF (20 ml) is added potassium carbonate (291 mg). The mixture is stirred for 2 h at 100° C. and subsequently poured into ice-cold water. After stirring for 5 min the resulting precipitate is filtered off and dried in vacuo. The residue is purified by flash column chromatography [amino phase silica gel, elution gradient: cyclohexane/EtOAc, 100/0 to 50/50 (v/v)] to afford the title compound as a solid.

Workup

  1. additionsubsequently poured into ice-cold water
  2. stirringAfter stirring for 5 min the resulting precipitate
  3. filtrationis filtered off
  4. customdried in vacuo
  5. customThe residue is purified by flash column chromatography [amino phase silica gel, elution gradient: cyclohexane/EtOAc, 100/0 to 50/50 (v/v)]

Sources & evidence

ORD record
ord-de2e8defbc53483bb89dcfa84a12e11a
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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