Ammonium Hydroxide → HCID 68904398, compound

HRID 736355Notes

Reaction equation

HRID 736355 reaction equation
C(=[N:14][C:15]1[CH:20]=[C:19]([C:21]([C:23]2[C:31]3[C:30](Cl)=[N:29][CH:28]=[N:27][C:26]=3[N:25]([CH:33]([CH3:35])[CH3:34])[CH:24]=2)=[O:22])[CH:18]=[C:17]([O:36][CH3:37])[N:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[OH-].[NH4+:39]>O1CCOCC1>[NH2:39][C:30]1[C:31]2[C:23]([C:21]([C:19]3[CH:18]=[C:17]([O:36][CH3:37])[N:16]=[C:15]([NH2:14])[CH:20]=3)=[O:22])=[CH:24][N:25]([CH:33]([CH3:34])[CH3:35])[C:26]=2[N:27]=[CH:28][N:29]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86603158HCID 86603158, compound

Product 1

HCID 68904398HCID 68904398, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

[2-(Benzhydrylidene-amino)-6-methoxy-pyridin-4-yl]-(4-chloro-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (7.31 g, 14.3 mmol) was added to a solution of ammonium hydroxide (150 mL) in dioxane (150 mL) and stirred at 45° C. in a sealed tube for 12 h. The reaction mixture was concentrated in vacuo, dissolved in hot CH2Cl2 (150 mL), and washed with water (3×100 mL). The aqueous layer was extracted with CH2Cl2 (3×100 mL) and the combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to provide the title compound as a yellow solid (3.43 g, 73%). MS: 327.2 (MH−); HPLC Rf: 2.1 min. (HPLC method 2).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in hot CH2Cl2 (150 mL)
  3. washwashed with water (3×100 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-093967763a384e569e090facc5d4a4e8
Source dataset
uspto-grants-2009_09
Patent number
US07595325B2

Reaction notes

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