Hydrochloric Acid → HCID 11472819, compound

HRID 254163Notes

Reaction equation

HRID 254163 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:13]=2)=[O:9])[CH:5]=[C:4]([C:39]2[O:40][CH:41]=[CH:42][CH:43]=2)[N:3]=1.Cl.O1CCOCC1>CO>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][OH:19])[N:13]=2)=[O:9])[CH:5]=[C:4]([C:39]2[O:40][CH:41]=[CH:42][CH:43]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11353589HCID 11353589, compound

Product 1

HCID 11472819HCID 11472819, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-amino-6-(2-furyl)-N-(6-(triphenylmethoxymethyl)pyridin-2-ylmethyl)pyrimidine-4-carboxamide (3.41 g, 6 mmol) in MeOH (50 mL) was treated with 4-M HCl in dioxane (7.5 mL, 30 mmol), stirred at room temperature for 20 h and concentrated in vacuo. The residue was diluted with water (50 mL) basified with 5-M NaOH, extracted with EtOAc (2×25 mL) and the combined organic phase washed with brine (25 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (1.19 g, 61%) as a cream solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water (50 mL)
  3. extractionextracted with EtOAc (2×25 mL)
  4. washthe combined organic phase washed with brine (25 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95bcf4d4b7de4dacaf961b8089d7d9e6
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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