Aluminium lithium hydride → HCID 58148045, compound

HRID 1879928Notes

Reaction equation

HRID 1879928 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[C:8]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:21][N:9]2[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:13]([O:12][C:11]1[C:10](=[O:20])[N:9]2[CH:21]=[C:22]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[CH:23]=[CH:24][C:8]2=[N:7][C:6]=1[CH:4]=[O:5])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58147995HCID 58147995, compound

Product 1

HCID 58148045HCID 58148045, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Benzyloxy-7-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylic acid methoxy-methyl-amide (product of example 14, 112 mg, 0.264 mmol) was dissolved in THF (1 mL) and added to a stirred solution of LAH (14 mg, 0.369 mmol) in THF at −45° C. The reaction was warmed to room temperature and stirred for 2 days. After this time, the reaction was quenched by addition of water and the residue filtered through celite, washing with ether. The combined organic layers where extracted with 1M HCl. The aqueous layer was basified with saturated aqueous bicarbonate solution and extracted with EtOAc. The combined organic layers were washed with water and brine, then dried and concentrated. Purification was achieved by column chromatography to afford the product (25 mg, 26% yield) as a yellow solid.

Workup

  1. customAfter this time, the reaction was quenched by addition of water
  2. filtrationthe residue filtered through celite
  3. washwashing with ether
  4. extractionThe combined organic layers where extracted with 1M HCl
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with water and brine
  7. customdried
  8. concentrationconcentrated
  9. customPurification

Sources & evidence

ORD record
ord-5588484da82047f28f1cf24c86984438
Source dataset
uspto-grants-2012_11
Patent number
US08318732B2

Reaction notes

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