Aluminium lithium hydride → HCID 178484830, compound

HRID 525051Notes

Reaction equation

HRID 525051 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[C:16]2[C:15]([NH:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=O)OC(C)(C)C)[CH2:20][CH2:19]3)=[N:14][CH:13]=[N:12][C:11]=2[S:10][C:9]=1[CH3:32]>C1COCC1>[CH3:7][C:8]1[C:16]2[C:15]([NH:17][C@H:18]3[CH2:23][CH2:22][C@H:21]([NH:24][CH3:25])[CH2:20][CH2:19]3)=[N:14][CH:13]=[N:12][C:11]=2[S:10][C:9]=1[CH3:32]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178435034HCID 178435034, compound

Product 1

HCID 178484830HCID 178484830, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

To a mixture of LiAlH4 (160 mg, 2.1 mmol, 5.0 eq) in THF (5 mL) was added a solution of tert-butyl trans-4-(5,6-dimethylthieno[2,3-d]pyrimidin-4-ylamino)cyclohexylcarbamate (160 mg, 0.42 mmol, 1.0 eq) in THF (5 mL). The mixture was stirred at 80° C. for 2 hours. The reaction was quenched with a mixture of THF/H2O and filtered. The cake was washed with CH2Cl2. The filtrate was concentrated and the residue was purified by column chromatography (CH2Cl2/MeOH/Et3N=20:1:0.5) on silica gel to give desired product compound I-44 as a white solid (72 mg, 60%). 1H NMR (400 MHz, CDCl3) δ 1.18-1.25 (m, 4H), 1.47 (br s, 2H), 1.95-1.98 (m, 2H), 2.16-2.18 (m, 2H), 2.34 (s, 3H), 2.38 (s, 3H), 2.39 (s, 3H), 4.02-4.08 (m, 1H), 5.23 (m, 1H), 8.23 (s, 1H). MS: m/z 291.2 (M+H)+.

Workup

  1. customThe reaction was quenched with a mixture of THF/H2O
  2. filtrationfiltered
  3. washThe cake was washed with CH2Cl2
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (CH2Cl2/MeOH/Et3N=20:1:0.5) on silica gel

Sources & evidence

ORD record
ord-e33ab885b7f34c8f860dbe528539a618
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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