Lithium aluminum hydride → HCID 57973940, compound

HRID 1863983Notes

Reaction equation

HRID 1863983 reaction equation
[Li+].[AlH4-].C(OC(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[NH:24][C:16]2[N:17]=[CH:18][N:19]=[C:20]([N:21]([CH3:23])[CH3:22])[C:15]=2[CH:14]=1)C.[C:26](OCC)(=[O:28])C.CO>C1COCC1>[CH3:22][N:21]([CH3:23])[C:20]1[C:15]2[CH:14]=[C:13]([C:8]3[CH:7]=[CH:12][C:11]([CH2:26][OH:28])=[CH:10][CH:9]=3)[NH:24][C:16]=2[N:17]=[CH:18][N:19]=1

Participants

5

Reactant 3

HCID 28112Lithium aluminum hydrideHCID 21584119Ethylacetate methanolHCID 86612958HCID 86612958, compound

Product 1

HCID 57973940HCID 57973940, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Li[AlH4] (660 mg, 17.40 mmol) is suspended in THF (70 mL). The suspension is cooled in an ice bath and small portions of 4-(4-Dimethylamino-7H-pyrrolo[2,3-d]pyrimidin-6-yl-benzoic acid ethylester are added under an argon atmosphere. The reaction is stirred for 30 min. at room temperature and then heated to 50° C. for additional 30 min. It is then cooled to room temperature again and quenched by careful addition of dilute aqueous NaOH solution. The resulting suspension is stirred for 30 min. and then all inorganic salts are removed by filtration. The remainig solution is concentrated in vacuo to give a yellow solid which is titurated with hexanes. The product is isolated by filtration and dried in vacuo to give a white powder. C15H16N4O: M+H=269.1; 1H-NMR (400 MHz, DMSO-d6): 13.01 (s, 1H, NH), 8.23 (s, 1H), 7.89 (d, 2H), 7.39 (d, 2H), 7.19 (s, 1H), 5.21 (s, 1H, OH), 4.55 (d, 2H), 3.35 (s, 6H). m. p.=306-309° C. Rf (ethyl acetate/MeOH 9:1)=0.30.

Workup

  1. temperatureThe suspension is cooled in an ice bath
  2. temperatureheated to 50° C. for additional 30 min
  3. temperatureIt is then cooled to room temperature again
  4. customquenched by careful addition of dilute aqueous NaOH solution
  5. stirringThe resulting suspension is stirred for 30 min.
  6. customall inorganic salts are removed by filtration
  7. concentrationThe remainig solution is concentrated in vacuo
  8. customto give a yellow solid which
  9. customThe product is isolated by filtration
  10. customdried in vacuo
  11. customto give a white powder

Sources & evidence

ORD record
ord-e6704fccfd5a4426bc6a0b04153c78c2
Source dataset
uspto-grants-2009_12
Patent number
US07625894B2

Reaction notes

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