Diisopropylethylamine → HCID 25211740, compound

HRID 2065580Notes

Reaction equation

HRID 2065580 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([NH:15][C:16]3[CH:17]=[C:18]([NH2:23])[C:19]([CH3:22])=[N:20][CH:21]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1.ClC(Cl)(O[C:28](=[O:34])OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C.[CH3:45][N:46]1[C:50]([NH2:51])=[CH:49][CH:48]=[N:47]1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([NH:15][C:16]3[CH:17]=[C:18]([NH:23][C:28]([NH:51][C:50]4[N:46]([CH3:45])[N:47]=[CH:48][CH:49]=4)=[O:34])[C:19]([CH3:22])=[N:20][CH:21]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 58171954N5-[5-(4-methoxy-phenyl)-pyrimidin-2-yl]-2-methyl-pyridine-3,5-diamine

Product 1

HCID 25211740HCID 25211740, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-(4-methoxyphenyl)pyrimidin-2-yl)-6-methylpyridine-3,5-diamine 12 (0.06 mmol) in THF (2 mL) is added triphosgene (0.02 mmol) and DIEA (0.01 mmol). The reaction is stirred at it for 15 min then 1-methyl-1H-pyrazol-5-amine (0.1 mmol) is added and stirring continued for 2 h. The reaction is reduced to dryness and purified by silica gel chromatography with DCM:MeOH=95:5 as eluant to afford 1-(5-(5-(4-methoxyphenyl)pyrimidin-2-ylamino)-2-methylpyridin-3-yl)-3-(1-methyl-1H-pyrazol-5-yl)urea C2 as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.72 (d, J=2.0 Hz, 1H), 8.70 (s, 2H), 8.60 (d, J=2.0 Hz, 1H), 7.54 (d, J=6.5 Hz, 2H), 7.40 (d, J=2.0 Hz, 1H), 7.03 (d, J=6.5 Hz, 2H), 6.28 (d, J=2.0 Hz, 1H), 3.84 (s, 3H), 3.79 (s, 3H), 2.49 (s, 3H). MS (m/z) (M+1)+: 431.2.

Workup

  1. stirringstirring
  2. waitcontinued for 2 h
  3. custompurified by silica gel chromatography with DCM

Sources & evidence

ORD record
ord-825634c1d920417ebd0e0bb36ee5a449
Source dataset
uspto-grants-2012_10
Patent number
US08288540B2

Reaction notes

Loading…