Sodium sulfate decahydrate → HCID 66589110, compound

HRID 1092200Notes

Reaction equation

HRID 1092200 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([N:9]3[CH:17]=[N:16][C:15]4[C:10]3=[N:11][C:12]([NH:23][C@H:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH3:25])=[N:13][C:14]=4[C:18](OCC)=[O:19])[CH:5]=2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([N:9]3[CH:17]=[N:16][C:15]4[C:10]3=[N:11][C:12]([NH:23][C@H:24]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH3:25])=[N:13][C:14]=4[CH2:18][OH:19])[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 66589137HCID 66589137, compound

Product 1

HCID 66589110HCID 66589110, compoundYield 331.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 9-(5-cyclopropyl-1H-pyrazol-3-yl)-2-[(S)-1-(4-fluorophenyl)ethylamino]-9H-purine-6-carboxylate (Example 11; 0.03 g, 0.069 mmol) in THF (3 ml) was cooled to 0° C. To which was slowly added lithium aluminium hydride (1.0 M in THF, 0.076 ml, 1.1 eq.). The reaction mixture was stirred at 0° C. for 30 minutes, at which point sodium sulfate decahydrate was added until bubbling stopped. The reaction was then filtered through a plug of celite, washed with THF (3×30 ml), and concentrated. The resulting residue was purified by column chromatography (DCM:MeOH=15:1) to give the title compound (0.09 g, 33%). NMR (400 MHz, CDCl3) 8.27 (s, 1H), 7.39-7.36 (m, 2H), 7.03-6.98 (m, 2H), 6.32 (s, 1H), 5.65-5.64 (m, 1H), 5.10-5.07 (m, 1H), 5.03 (s, 2H), 3.87-3.85 (m, 1H), 1.93-1.88 (m, 1H), 1.57 (d, J=6.8 Hz, 3H), 1.08-1.06 (m, 2H), 0.81-0.77 (m, 2H). MS: Calcd.: 393; Found: [M+H]+ 394.

Workup

  1. additionwas added
  2. customuntil bubbling
  3. filtrationThe reaction was then filtered through a plug of celite
  4. washwashed with THF (3×30 ml)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by column chromatography (DCM:MeOH=15:1)

Sources & evidence

ORD record
ord-1753cd52f6974462b9a473c616ad2da7
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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