Diisopropylethylamine → 5-Chloro-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 1641391Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:18][C:19]2[CH:23]=[C:22](OC(C)C)[NH:21][N:20]=2)=[N:4][C:5]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[CH3:10])=[N:6][CH:7]=1.Cl[C:29]1N=C(NC2C=C(C)NN=2)C(Cl)=CN=1.CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[C:3]([NH:18][C:19]2[CH:23]=[C:22]([CH3:29])[NH:21][N:20]=2)=[N:4][C:5]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[CH3:10])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of (S)-1-(5-fluoropyridin-2-yl)ethanamine (Method 6; 146 mg, 1.04 mmol), 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (Method 38; 244 mg, 1.04 mmol) and DIEA (0.39 ml) in n-BuOH (3 ml) was charged into a microwave reaction vessel. The vessel was sealed and heated in microwave reactor at 160° C. for 6 hrs. The solvent was removed under reduced pressure and the residue was purified by Gilson (10-50% acetonitrile/H2O, 15 min) to give the title compound as solid (489 mg). 1H NMR: 12.02 (s, 1H), 8.50 (d, 1H), 7.87-7.97 (m, 114), 7.64 (ddd, 1H), 7.33-7.46 (m, 1H), 5.85 (s, 1H), 4.75-5.24 (m, 1H), 2.16-2.21 (m, 3H), 1.45 (d, 3H); m/z 349.

Workup

additionwas charged into a microwave reaction vessel
customThe vessel was sealed
customThe solvent was removed under reduced pressure
customthe residue was purified by Gilson (10-50% acetonitrile/H2O, 15 min)

Sources & evidence

ORD record: ord-f4df2297804c43bd9804e0f40b15aa28
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114989B2

Reaction notes

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