Hydrochloric Acid → 3-hydroxy-2-hydroxymethyl-2-methyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 1677394Notes

Reaction equation

HRID 1677394 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:14]=[C:15]3[C:21]([C:22]([C:24]4([CH3:32])[CH2:29][O:28]C(C)(C)[O:26][CH2:25]4)=[O:23])=[CH:20][NH:19][C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].Cl>O1CCCC1.CO>[OH:26][CH2:25][C:24]([CH2:29][OH:28])([CH3:32])[C:22]([C:21]1[C:15]2[C:16](=[N:17][CH:18]=[C:13]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)[N:14]=2)[NH:19][CH:20]=1)=[O:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 44206487HCID 44206487, compound

Product 1

HCID 497643143-hydroxy-2-hydroxymethyl-2-methyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-oneYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of [2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(2,2,5-trimethyl-[1,3]dioxan-5-yl)-methanone (30 mg, 0.7 mmol) in tetrahydrofuran (5 ml) and MeOH (4 ml) was heated using a heat gun until homogeneity was achieved. The reaction mixture was treated with 1M HCl (1.0 ml, 1.0 mmol) and stirred for 1 hour. The reaction mixture was concentrated to 3 ml of solvent and then partitioned between EtOAc/saturated aqueous NaHCO3. The organic layers were collected, dried over MgSO4, filtered, and concentrated affording 20 mg (73%) of 3-hydroxy-2-hydroxymethyl-2-methyl-1-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as a pale yellow solid. MP 222-223° C., M+H=402.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated to 3 ml of solvent
  3. custompartitioned between EtOAc/saturated aqueous NaHCO3
  4. customThe organic layers were collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fc4d410b390647fca891f6de4b4cbd73
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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