Dimethyl acetylenedicarboxylate → HCID 136502909, compound

HRID 1477512Notes

Reaction equation

HRID 1477512 reaction equation
[NH2:1]/[C:2](=[N:15]\O)/[C:3]([NH:6][C:7]([C:9]1[O:10][C:11]([CH3:14])=[N:12][N:13]=1)=[O:8])([CH3:5])[CH3:4].[C:17]([C:23]([O:25][CH3:26])=[O:24])#[C:18][C:19](OC)=[O:20].C([O:31]C)(C)(C)C>CO>[CH3:14][C:11]1[O:10][C:9]([C:7]([NH:6][C:3]([C:2]2[NH:1][C:19](=[O:20])[C:18]([OH:31])=[C:17]([C:23]([O:25][CH3:26])=[O:24])[N:15]=2)([CH3:5])[CH3:4])=[O:8])=[N:13][N:12]=1

Participants

5

Reactant 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 15413tert-Butyl methyl etherHCID 89655910HCID 89655910, compound

Product 1

HCID 136502909HCID 136502909, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

N-[(1Z)-1-amino-1-(hydroxyimino)-2-methylpropan-2-yl]-5-methyl-1,3,4-oxadiazole-2-carboxamide (IVa) (198 gms) was suspended in methanol (1188 ml) and cooled to 15 to 25° C. Dimethyl acetylenedicarboxylate (DMAD; 152.8 gms) was added and the reaction mass was stirred for 2 to 3 hours at 25° C. The reaction mass was concentrated under reduced pressure and xylene was added and stirred between 135° C. and 125° C. for 6 hour. After completion of reaction, the mixture was cooled to 60° C. and methanol (170 ml) & methyl tert-butyl ether (MTBE) were added to the reaction mass and stirred for 1 hour. The resultant slurry was filtered and washed with a 9:1 mixture of methanol & methyl tert-butyl ether (MTBE) and dried to give methyl 2-(2-(5-methyl-1,3,4-oxadiazole-2-carboxamido)propan-2-yl)-1,6-dihydro-5-hydroxy-6-oxopyrimidine-4-carboxylate (Va).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure and xylene
  2. additionwas added
  3. stirringstirred between 135° C. and 125° C. for 6 hour
  4. customAfter completion of reaction
  5. temperaturethe mixture was cooled to 60° C.
  6. stirringstirred for 1 hour
  7. filtrationThe resultant slurry was filtered
  8. washwashed with a 9:1 mixture of methanol & methyl tert-butyl ether (MTBE)
  9. customdried

Sources & evidence

ORD record
ord-8e749c9daf074b2692bd08a29909bec3
Source dataset
uspto-grants-2016_08
Patent number
US09403809B2

Reaction notes

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