Aluminium lithium hydride → HCID 67120140, compound

HRID 2042217Notes

Reaction equation

HRID 2042217 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[CH:16][C:17]4[S:22][CH:21]=[C:20]([C:23]5[CH:33]=[CH:32][C:26]([C:27](OCC)=[O:28])=[CH:25][CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[CH:16][C:17]4[S:22][CH:21]=[C:20]([C:23]5[CH:33]=[CH:32][C:26]([CH2:27][OH:28])=[CH:25][CH:24]=5)[C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67120141HCID 67120141, compound

Product 1

HCID 67120140HCID 67120140, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(2-(6-morpholinopyridin-3-ylamino)thieno[3,2-d]pyrimidin-7-yl)benzoate (150 mg, 0.33 mmol) was dissolved in anhydrous tetrahydrofuran (1.5 mL) and lithium aluminum hydride 2.0 M tetrahydrofuran (0.25 mL, 0.50 mmol) solution was slowly added at 0° C. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction mixture was diluted with ethyl ether (2.0 mL). The remaining lithium aluminum hydride was removed by adding water very slowly. After adding magnesium sulfate, the mixture was concentrated by filtering. The resultant target compound (130 mg, 95% yield) was used in the following reaction without purification.

Workup

  1. customUpon completion of the reaction
  2. customThe remaining lithium aluminum hydride was removed
  3. additionby adding water very slowly
  4. additionAfter adding magnesium sulfate
  5. concentrationthe mixture was concentrated
  6. filtrationby filtering

Sources & evidence

ORD record
ord-b5d782bba9ee4989bd9058c2fcad6990
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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