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

HRID 2201184Notes

Reaction equation

HRID 2201184 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][NH:9][C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[C:6]2[C:5](=[O:19])[N:4]([CH3:20])[C:3]1=[O:21].Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[C:14]([C:13]1[CH:12]=[C:11]([C:10]2[N:9]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:8]=[C:7]3[C:6]=2[C:5](=[O:19])[N:4]([CH3:20])[C:3](=[O:21])[N:2]3[CH3:1])[CH:18]=[CH:17][CH:16]=1)#[N:15]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 867229283-(1,3-Dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

Product 1

HCID 86723425Methyl 4-(5-(3-cyanophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)butanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (step 4) (300 mg, 1.07 mmol), methyl 4-bromobutanoate (291 mg, 1.61 mmol) and cesium carbonate (697 mg, 2.14 mmol) in DMF (4 mL) was stirred at 80° C. for 2 hours. The reaction mixture was diluted with ethyl acetate (20 mL) and was washed with 1M HCl (3×10 mL). After the third wash, the mixture was concentrated in vacuo. The residue was triturated with diethyl ether and dried under vacuum at 50° C.

Workup

  1. washwas washed with 1M HCl (3×10 mL)
  2. washAfter the third wash
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was triturated with diethyl ether
  5. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-f25dd7ab70e24a04a0f1ac7eda9092a6
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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