Sodium Carbonate → 1-(2-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)phenyl)prop-2-en-1-ol

HRID 1484997Notes

Reaction equation

[CH:1]([CH:3]1[O:7]B(O)[C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]1=2)=[CH2:2].Br[C:14]1[N:19]=[C:18]([NH:20][C:21]2[CH:25]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[NH:23][N:22]=2)[C:17]([Cl:29])=[CH:16][N:15]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:17]1[C:18]([NH:20][C:21]2[CH:25]=[C:24]([CH:26]3[CH2:28][CH2:27]3)[NH:23][N:22]=2)=[N:19][C:14]([C:5]2[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=2[CH:3]([OH:7])[CH:1]=[CH2:2])=[N:15][CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of 3-vinylbenzo[c][1,2]oxaborol-1(3H)-ol (2.2 g, 13.4 mmol, 1.3 eq), 2-bromo-5-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (3.3 g, 10.5 mmol, 1.0 eq), Pd(PPh3)4 (1.3 g, 1.1 mmol, 0.11 equiv.) and saturated aq Na2CO3 (5 mL) in 1,4-dioxane (30 mL) was stirred at 90° C. for 3 h under N2, then, cooled to rt and partitioned between EtOAc and water. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 1-(2-(5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)phenyl)prop-2-en-1-ol (1.8 g, 47%). LC-MS (m/z)=368.0 [M+H]+.

Workup

temperaturecooled to rt
custompartitioned between EtOAc and water
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-874a269848824d26a8bb3fef490e5690
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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