4,6-dichloro-N-methyl-N-(prop-2-yn-1-yl)pyrimidine-5-carboxamide → 4-Chloro-1,2-dihydro-2-methyl-3H-pyrrolo[3,4-c]pyridin-3-one

HRID 511557Notes

Reaction equation

HRID 511557 reaction equation
ClC1[C:7]([C:8]([N:10]([CH3:14])[CH2:11][C:12]#[CH:13])=[O:9])=[C:6]([Cl:15])[N:5]=[CH:4]N=1>[N+](C1C=CC=CC=1)([O-])=O>[Cl:15][C:6]1[C:7]2[C:8](=[O:9])[N:10]([CH3:14])[CH2:11][C:12]=2[CH:13]=[CH:4][N:5]=1

Participants

3

Reactant 1

HCID 121631394,6-dichloro-N-methyl-N-(prop-2-yn-1-yl)pyrimidine-5-carboxamide2×

Product 1

HCID 121631514-Chloro-1,2-dihydro-2-methyl-3H-pyrrolo[3,4-c]pyridin-3-oneYield 56%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

A solution of 4,6-dichloro-N-methyl-N-(prop-2-yn-1-yl)pyrimidine-5-carboxamide (Compound 310F, 7.6 g, 31 mmol) in Nitrobenzene (76 mL) was evacuated and purged with argon (3×). The reaction mixture was irradiated in the microwave for 1.5 minutes at 250° C. The reaction mixture was filtered through a pad of celite. The nitrobenzene solution was passed through a silica gel plug and washed with DCM to remove the nitrobenzene. The silica was then washed with DCM/MeOH solution (90:10). The filtrated was concentrated under reduced pressure to yield a red solid. The crude material was purified by silica gel chromatography on a combi-flash Rf system using DCM/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield an orange solid (3.1598 g, 56%). 1H NMR (DMSO-d6, 400 MHz): δ=8.53 (d, J=5.05 Hz, 1H), 7.70 (d, J=5.05 Hz, 1H), 4.53 (s, 2H), 3.05 (s, 3H). MS (ES+): m/z 183.02 [MH+] (TOF, polar).

Workup

  1. custompurged with argon (3×)
  2. customThe reaction mixture was irradiated in the microwave for 1.5 minutes at 250° C
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. washwashed with DCM
  5. customto remove the nitrobenzene
  6. washThe silica was then washed with DCM/MeOH solution (90:10)
  7. concentrationThe filtrated was concentrated under reduced pressure
  8. customto yield a red solid
  9. customThe crude material was purified by silica gel chromatography on a combi-flash Rf system
  10. additionThe fractions containing product
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eee81e1edbc64c3480d7abf911618445
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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