Hydrochloric Acid → 4-(9-isopropyl-9H-purin-6-yl)phenol

HRID 1518333Notes

Reaction equation

HRID 1518333 reaction equation
[CH:1]([N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][CH:7]=[N:8][C:9]=2[C:13]1[CH:18]=[CH:17][C:16]([O:19]C2CCCCO2)=[CH:15][CH:14]=1)([CH3:3])[CH3:2].Cl>O1CCOCC1>[CH:1]([N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][CH:7]=[N:8][C:9]=2[C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 594476359-isopropyl-6-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-9H-purine

Product 1

HCID 1360277224-(9-isopropyl-9H-purin-6-yl)phenolYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 52C (149 mg, 0.44 mmol) in dioxane (3 ml) was treated with HCl (4N in dioxane) (0.55 ml, 2.2 mmol) and stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and dried to give a light gray solid 52D in 94% yield: 1H NMR (300 MHz, DMSO-d6) δ ppm 10.16 (1H, s), 8.90 (1H, s), 8.76 (1H, m), 8.73 (2H, m), 6.97 (2H, m), 4.91 (1H, septet), 1.60 (6H, d).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdried

Sources & evidence

ORD record
ord-e8280ba7167d4875a800d7867813e10c
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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