Diisopropylethylamine → HCID 53468239, compound

HRID 1958339Notes

Reaction equation

HRID 1958339 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][N:10]3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][N:26]=1)[C:21](O)=[O:22].CCCP(=O)=O.C(N(C(C)C)C(C)C)C>O1CCCC1.C(OCC)(=O)C>[CH3:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][N:26]=1)[C:21]([NH:15][C:13]1[CH:12]=[CH:11][N:10]2[CH:16]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[C:9]2[N:14]=1)=[O:22]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27628212-Methylpyridine-4-carboxylic acidHCID 16167369Propylphosphoric anhydrideHCID 508783902-Phenylimidazo[1,2-A]pyrimidin-7-amine

Product 1

HCID 53468239HCID 53468239, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (156 mg, 0.766 mmol, 1 eq.), 2-methylisonicotinic acid (116 mg, 0.842 mmol, 1.1 eq.), propylphosphonic anhydride in ethyl acetate 50% (1.13 ml, 1.91 mmol, 2.5 eq) and ethyldiisopropylamine (0.535 ml, 3.06 mmol, 4 eq) in tetrahydrofuran (10 ml) is stirred for 18 hours at roomtemperature. The solution is then refluxed for 4 hours. The mixture is diluted with ethyl acetate and washed with sat. aqueous sodium bicarbonate, with water, dried over magnesium sulfate and the solvent is removed in vacuo. Purification of the residue by chromatography on a 12 g RediSep silica cartridge using dichloromethane+5% methanol as eluent affords 2-methyl-N-(2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-isonicotinamide (45 mg, 17.8%) as a yellow solid. MS: m/e=330.2 (M+H+)

Workup

  1. temperatureThe solution is then refluxed for 4 hours
  2. washwashed with sat. aqueous sodium bicarbonate, with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is removed in vacuo
  5. customPurification of the residue by chromatography on a 12 g RediSep silica cartridge

Sources & evidence

ORD record
ord-6229651517534d44b00c360481678889
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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