Ammonium Hydroxide → 4-(2-Amino-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 338705Notes

Reaction equation

HRID 338705 reaction equation
CS([C:4]1[N:5]=[CH:6][C:7]2[CH2:12][N:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)=[O:20])[CH:14]=3)[CH2:10][C:8]=2[N:9]=1)=O.CS(C1[N:37]=CC2CN(C3C=CN=C(C(NC4C=CC=C(C(F)(F)F)C=4)=O)C=3)CC=2N=1)(=O)=O.[OH-].[NH4+]>O1CCOCC1>[F:29][C:28]([F:31])([F:30])[C:24]1[CH:23]=[C:22]([NH:21][C:19]([C:15]2[CH:14]=[C:13]([N:11]3[CH2:12][C:7]4[CH:6]=[N:5][C:4]([NH2:37])=[N:9][C:8]=4[CH2:10]3)[CH:18]=[CH:17][N:16]=2)=[O:20])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 14923Ammonium Hydroxide2×HCID 866958324-(2-(Methylsulfinyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamideHCID 866958334-(2-(methylsulfonyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide

Product 1

HCID 866958314-(2-Amino-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-(Methylsulfinyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide and 4-(2-(methylsulfonyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide was suspended in 1,4-dioxane (7 mL). Ammonium hydroxide (30%, 1.5 mL) was added and the reaction was heated at 90° C. for 16 hours. TLC indicated only partial conversion to the desired amine. The solvent was reduced with a nitrogen stream and then additional ammonium hydroxide (1 mL) was added. The reaction was sealed in a tube and heated at 100° C. for 17 h. The solvent was evaporated in vacuo. The resulting solid was triturated with water and then methanol. The solid was chromatographed on silica gel (4 g) eluted with ethyl acetate:methanol (9:1) to give the title compound (10.6 mg, 0.026 mmol).

Workup

  1. customThe reaction was sealed in a tube
  2. temperatureheated at 100° C. for 17 h
  3. customThe solvent was evaporated in vacuo
  4. customThe resulting solid was triturated with water
  5. customThe solid was chromatographed on silica gel (4 g)
  6. washeluted with ethyl acetate:methanol (9:1)

Sources & evidence

ORD record
ord-14dc479da9954d54b37381588e890346
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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