Aluminium lithium hydride → HCID 118599143, compound

HRID 1050378Notes

Reaction equation

HRID 1050378 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)[C:11](=[O:21])[N:10]2[C:22]([CH2:31][C:32](OC)=[O:33])([CH2:26][C:27](OC)=[O:28])[NH:23][C:24](=[O:25])[C:9]=12>O1CCCC1>[Cl:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)[C:11](=[O:21])[N:10]2[C:22]([CH2:26][CH2:27][OH:28])([CH2:31][CH2:32][OH:33])[NH:23][C:24](=[O:25])[C:9]=12

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 118599006HCID 118599006, compound

Product 1

HCID 118599143HCID 118599143, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of lithium aluminum hydride (71 mg, 1.9 mmol) in tetrahydrofuran (3 mL) at 0° C. a solution of dimethyl 2,2′-(8-chloro-1,5-dioxo-6-(pyrimidin-4-ylamino)-1,2,3,5-tetrahydroimidazo[1,5-a]pyridine-3,3-diyl)diacetate (5, 280 mg, 0.66 mmol) in tetrahydrofuran (2 mL) was added slowly. After consumption of starting material the reaction mixture was quenched with 10% sodium hydroxide solution (1 mL), diluted with 10 ml of ethyl acetate. The organic layer was separated and dried over anhydrous sodium sulfate and concentrated under reduce pressure to afford the residue. The residue was purified prep HPLC to afford 8-chloro-3,3-bis(2-hydroxyethyl)-6-(pyrimidin-4-ylamino)-2,3-dihydroimidazo[1,5-a]pyridine-1,5-dione (Cpd. No. 153) as yellow solid. Yield: 0.047 g, 19%; MS (ESI) m/z 366.09 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ 9.58-9.57 (brs, 1H), 8.83 (s, 1H), 8.75 (s, 1H), 8.42 (d, J=5.6 Hz, 1H), 7.44-7.42 (d, J=5.6 Hz, 1H), 4.44 (brs, 2H), 3.34-3.26 (m, 4H), 2.79-3.73 (m, 2H), 2.11-2.08 (m, 2H).

Workup

  1. customAfter consumption of starting material the reaction mixture
  2. customwas quenched with 10% sodium hydroxide solution (1 mL)
  3. additiondiluted with 10 ml of ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto afford the residue
  8. customThe residue was purified prep HPLC

Sources & evidence

ORD record
ord-6343f9c56bfb438496e1cea63afcf38c
Source dataset
uspto-grants-2016_07
Patent number
US09382248B2

Reaction notes

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