Methyl Acrylate → Methyl 3-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate

HRID 2201232Notes

Reaction equation

HRID 2201232 reaction equation
C1CCN2C(=NCCC2)CC1.[CH3:12][N:13]1[C:18]2=[CH:19][NH:20][C:21]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])=[C:17]2[C:16](=[O:30])[N:15]([CH3:31])[C:14]1=[O:32].[C:33]([O:37][CH3:38])(=[O:36])[CH:34]=[CH2:35]>C(#N)C>[C:25]([C:24]1[CH:23]=[C:22]([C:21]2[N:20]([CH2:35][CH2:34][C:33]([O:37][CH3:38])=[O:36])[CH:19]=[C:18]3[C:17]=2[C:16](=[O:30])[N:15]([CH3:31])[C:14](=[O:32])[N:13]3[CH3:12])[CH:29]=[CH:28][CH:27]=1)#[N:26]

Participants

5

Reactant 3

HCID 7294Methyl Acrylate2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 867229283-(1,3-Dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Product 1

HCID 90217878Methyl 3-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

DBU (0.656 mL, 4.35 mmol) was added to a solution of 3-(1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (Example 9 Step 4) (1.22 g, 4.35 mmol) and methyl acrylate (0.392 mL, 4.35 mmol) in acetonitrile (15 mL). The mixture was stirred at room temperature for 4 days. Further portions of methyl acrylate (0.392 mL, 4.35 mmol) and DBU (0.656 mL, 4.35 mmol) were added as required to allow the reaction to run to completion. The reaction was quenched with saturated NH4Cl(aq) and extracted with DCM (2×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 20-100% EtOAc/hexane afforded a crude material which was triturated with DCM/diethyl ether/hexane to afford the title compound.

Workup

  1. customthe reaction
  2. customThe reaction was quenched with saturated NH4Cl(aq)
  3. extractionextracted with DCM (2×)
  4. customevaporated under vacuum
  5. customPurification by chromatography on silica
  6. washeluting with 20-100% EtOAc/hexane
  7. customafforded a crude material which
  8. customwas triturated with DCM/diethyl ether/hexane

Sources & evidence

ORD record
ord-2993b1d69e9f448f86d32619c4cd3a12
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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