Cesium carbonate → 3,3-Dimethyl-6-[(pyrimidin-4-yl)amino]-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione

HRID 1050329Notes

Reaction equation

HRID 1050329 reaction equation
Cl[C:2]1[C:7](=[O:8])[N:6]2[C:9]([CH3:14])([CH3:13])[NH:10][C:11](=[O:12])[C:5]2=[CH:4][CH:3]=1.COC1C=CC(CN2CCN3C(=O)C([NH:32][C:33]4[CH:38]=[CH:37][N:36]=[CH:35][N:34]=4)=CC=C3C2=O)=CC=1.CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[CH3:13][C:9]1([CH3:14])[N:6]2[C:7](=[O:8])[C:2]([NH:32][C:33]3[CH:38]=[CH:37][N:36]=[CH:35][N:34]=3)=[CH:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25112535BrettphosHCID 118598887HCID 118598887, compoundHCID 118598941HCID 118598941, compound

Product 1

HCID 1185987213,3-Dimethyl-6-[(pyrimidin-4-yl)amino]-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-3,3-dimethyl-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (4, 0.25 g, 1.18 mmol) in 1,4-dioxane (8 mL), pyrimidin-4-amine (5, 0.14 g, 1.41 mmol), Brettphos (0.19 g, 0.23 mmol) and cesium carbonate (0.76 g, 2.36 mmol) were added and the reaction mixture was degassed with argon for 5 min. Tris dibenzylideneacetone dipalladium (0) (0.11 g, 0.12 mmol) was added. The reaction was degassed with argon for another 5 min and then stirred at 100° C. for 10 h. The reaction mixture was cooled to room temperature, filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 5% methanol in dichloromethane to afford 3,3-dimethyl-6-(pyrimidin-4-ylamino)-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (Cpd. No. 2) as a light yellow solid. Yield: 0.036 g, 11%; MS (ESI) m/z 272[M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.70 (s, 1H), 9.42 (s, 1H), 8.81-8.73 (m, 2H), 8.37 (d, J=5.9 Hz, 1H), 7.40-7.34 (m, 1H), 6.87 (d, J=7.7 Hz, 1H), 1.82 (s, 6H).

Workup

  1. customthe reaction mixture was degassed with argon for 5 min
  2. customThe reaction was degassed with argon for another 5 min
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8b55e7b53611490c96eca38b946ccc24
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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