Sodium Hydroxide → 1459230-34-2

HRID 1750328Notes

Reaction equation

HRID 1750328 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-:13].[Na+]>O1CCOCC1>[I:11][C:10]1[C:3]2[C:2](=[O:13])[NH:7][CH:6]=[N:5][C:4]=2[N:8]([CH3:12])[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 426094624-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 1365990221459230-34-2

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (19.0 g, 64.9 mmol) in 1,4-dioxane (481 ml) was added 2M sodium hydroxide (aq) solution (479 ml, 959 mmol). The solution was heated to 100° C. and heated for 4 h. The solution was cooled. The organic solvent was removed in vacuo. The aqueous was acidified to ca pH 4 using concentrated hydrochloric acid. The resulting suspension was filtered and dried under vacuum and flowing nitrogen to afford the title compound which was used without further purification (15.7 g, 88%). LCMS RT=0.65 min, M+H+=276.0. 1H NMR (500 MHz, d6-DMSO) 11.93 (br s, 1H), 7.90 (s, 1H), 3.68 (s, 3H).

Workup

  1. temperatureheated for 4 h
  2. temperatureThe solution was cooled
  3. customThe organic solvent was removed in vacuo
  4. filtrationThe resulting suspension was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d2c5e0ab829447b4b290bba154367db1
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Reaction notes

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