1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → HCID 178429766, compound

HRID 1050336Notes

Reaction equation

HRID 1050336 reaction equation
[CH:1]1([C:4]2[N:5](COCC[Si](C)(C)C)[C:6]3[C:11]([N:12]=2)=[C:10]([NH:13][C:14]2[C:19](=[O:20])[N:18]4[C:21]([CH3:29])([C:25]([F:28])([F:27])[F:26])[NH:22][C:23](=[O:24])[C:17]4=[CH:16][CH:15]=2)[N:9]=[CH:8][N:7]=3)[CH2:3][CH2:2]1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:1]1([C:4]2[NH:5][C:6]3[C:11]([N:12]=2)=[C:10]([NH:13][C:14]2[C:19](=[O:20])[N:18]4[C:21]([CH3:29])([C:25]([F:26])([F:28])[F:27])[NH:22][C:23](=[O:24])[C:17]4=[CH:16][CH:15]=2)[N:9]=[CH:8][N:7]=3)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 131736064HCID 131736064, compound

Product 1

HCID 178429766HCID 178429766, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-[[8-cyclopropyl-9-(2-trimethylsilylethoxymethyl)purin-6-yl]amino]-3-methyl-3-(trifluoromethyl)-2H-imidazo[1,5-a]pyridine-1,5-dione (8, 0.25 g, 0.47 mmol) in tetrahydrofuran (50 mL) was added tetrabutylammonium fluoride hydrate (0.61 g, 2.33 mmol). The mixture was heated at 70° C. for 4 h. After TLC showed consumption of 8, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The crude mixture was purified via column chromatography (silica, methanol/dichloromethane=2%) to afford 6-[(8-cyclopropyl-9H-purin-6-yl)amino]-3-methyl-3-(trifluoromethyl)-2H-imidazo[1,5-a]pyridine-1,5-dione (Cpd. No. 37) as yellow solid. Yield: 135 mg, 71%; MS (ESI) m/z 406.29 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 13.24 (s, 1H), 10.55 (s, 1H), 8.80 (d, J=7.6 Hz, 1H), 8.64 (s, 1H), 8.49 (s, 1H), 7.10 (d, J=7.6 Hz, 1H), 2.16 (m, 1H), 2.15 (s, 3H), 1.12 (m, 4H).

Workup

  1. customconsumption of 8
  2. additionthe reaction mixture was diluted with water (50 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified via column chromatography (silica, methanol/dichloromethane=2%)

Sources & evidence

ORD record
ord-ec22eeb23e8c4e209245a34f4c9a740f
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

Loading…