Ammonia → HCID 86590949, compound

HRID 459985Notes

Reaction equation

HRID 459985 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3=[N:20][C:21](S(C)=O)=[N:22][CH:23]=[C:18]3[CH2:17][N:16]([C:27]3[C:32]([F:33])=[C:31]([O:34][CH3:35])[CH:30]=[C:29]([O:36][CH3:37])[C:28]=3[F:38])[C:15]2=[O:39])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:40]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:19]3=[N:20][C:21]([NH2:40])=[N:22][CH:23]=[C:18]3[CH2:17][N:16]([C:27]3[C:32]([F:33])=[C:31]([O:34][CH3:35])[CH:30]=[C:29]([O:36][CH3:37])[C:28]=3[F:38])[C:15]2=[O:39])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86760471HCID 86760471, compound

Product 1

HCID 86590949HCID 86590949, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-7-methylsulfinyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (419 mg, 0.738 mmol) and liquid ammonia (20 mL) in dioxane (20 mL) were stirred in a sealed tube at room temperature for 24 hours. The solvent was removed under reduced pressure. The resulting residue was purified via flash chromatography eluting with a gradient of ethyl acetate:hexanes (2:1 to 5:1) to give 312 mg (81%) of the title compound: MS (APCI) 421.1, 465.2, 521.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe resulting residue was purified via flash chromatography
  3. washeluting with a gradient of ethyl acetate:hexanes (2:1 to 5:1)

Sources & evidence

ORD record
ord-137edcaca2ab4d6287c258fa4dd72e2e
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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