Aluminium lithium hydride → HCID 178484829, compound

HRID 2369382Notes

Reaction equation

HRID 2369382 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:29][C:6]2[C:7]3[C:12]([NH:13][C@H:14]4[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=O)OC(C)(C)C)[CH2:16][CH2:15]4)=[N:11][CH:10]=[N:9][C:8]=3[S:28][C:5]=2[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1([CH3:30])[CH2:29][C:6]2[C:7]3[C:12]([NH:13][C@H:14]4[CH2:15][CH2:16][C@H:17]([NH:20][CH3:21])[CH2:18][CH2:19]4)=[N:11][CH:10]=[N:9][C:8]=3[S:28][C:5]=2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178424111HCID 178424111, compound

Product 1

HCID 178484829HCID 178484829, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl trans-4-(6,6-dimethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-ylamino)cyclohexanylcarbamate (210 mg, 0.49 mmol) in 10 mL of THF was added LiAlH4 (88 mg, 2.44 mmol, 5.0 eq) carefully at 0° C. The resulting mixture was heated at reflux for 2 h and cooled down. The reaction was cooled to 0° C. and quenched with a mixture of THF/H2O. Extracted with EtOAc (3×20 mL) and the combined organics were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by column chromatography in silica gel (DCM/MeOH/NH4OH=100:8:1) to give the product as white solid (140 mg, 80%). 1H NMR (400 MHz, CDCl3) δ1.01 (s, 6H), 1.18-1.30 (m, 4H), 1.58 (t, J=6.4 Hz, 2H), 1.96 (br s, 1H), 1.98-2.01 (m, 2H), 2.17-2.19 (m, 2H), 2.38-2.40 (m, 1H), 2.41 (s, 3H), 2.56 (s, 2H), 2.73-2.76 (m, 2H), 4.07-4.10 (m, 1H), 5.01 (d, J=7.2 Hz, 1H), 8.29 (s, 1H). MS: m/z 345.1 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled down
  4. customquenched with a mixture of THF/H2O
  5. extractionExtracted with EtOAc (3×20 mL)
  6. dry with materialthe combined organics were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was purified by column chromatography in silica gel (DCM/MeOH/NH4OH=100:8:1)

Sources & evidence

ORD record
ord-a29f2e05872245538de6594d7ed10924
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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