Potassium Carbonate → HCID 57961849, compound

HRID 541863Notes

Reaction equation

HRID 541863 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([F:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]3[N:15]=[C:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=[CH:12][CH:11]=3)[CH:5]=[CH:6][CH:7]=2)[C:28]([F:32])=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 57961604HCID 57961604, compound

Product 1

HCID 57961849HCID 57961849, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl {6-[2-(3-aminophenyl)ethyl]pyridin-2-yl}carbamate (200 mg, 0.64 mmol) (prepared in Example C17, step B) and 2,4-dichloro-5-fluoropyrimidine (112 mg, 0.67 mmol) in N,N-dimethylformamide (2.9 mL) was added potassium carbonate (264 mg, 1.91 mmol). The resultant mixture was stirred overnight at room temperature. The reaction mixture was filtered first to remove K2CO3. The filtrate was concentrated to give the residue, which was purified by silica gel column chromatography to give the desired product as a light yellow gum (216 mg, 76%). LCMS for C22H24ClFN5O2 (M+H)+: m/z=444.0.

Workup

  1. filtrationThe reaction mixture was filtered first
  2. customto remove K2CO3
  3. concentrationThe filtrate was concentrated
  4. customto give the residue, which
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4bd6d2d4d99242bbae6f8dc3a1b38256
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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