Diisopropylethylamine → HCID 178493052, compound

HRID 415413Notes

Reaction equation

HRID 415413 reaction equation
Cl.[F:2][C:3]1[CH:4]=[N:5][C:6]([C@@H:9]([NH2:11])[CH3:10])=[N:7][CH:8]=1.Cl[C:13]1[N:18]=[C:17]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH3:26])[NH:22][N:21]=2)[CH:16]=[C:15]([Cl:27])[N:14]=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:27][C:15]1[N:14]=[C:13]([NH:11][C@H:9]([C:6]2[N:7]=[CH:8][C:3]([F:2])=[CH:4][N:5]=2)[CH3:10])[N:18]=[C:17]([NH:19][C:20]2[CH:24]=[C:23]([O:25][CH3:26])[NH:22][N:21]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66624037(S)-1-(5-Fluoropyrimidin-2-yl)ethanamine hydrochlorideHCID 1784930502,6-Dichloro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amine

Product 1

HCID 178493052HCID 178493052, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of (S)-1-(5-fluoropyrimidin-2-yl)ethanamine hydrochloride (Method 7, 512 mg), 2,6-dichloro-N-(5-methoxy-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 42, 682 mg) and DIPEA (1.16 ml) in n-BuOH (13 ml) was heated at 105° C. over night. The solvent was removed under reduced pressure and the residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes) to give the titled compound as solid (500 mg). 1H NMR δ 8.92 (s, 2H) 5.95 (s, 1H) 5.18 (s, 1H) 3.77 (s, 3H) 1.49 (d, 3H); m/z 366.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by Gilson (10-50% MeCN/H2O, 15 minutes)

Sources & evidence

ORD record
ord-6e33b1adbdb4420b9d4266a25983d569
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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