Potassium Phosphate, Tribasic → HCID 50943141, compound

HRID 1484835Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:17][S:18]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)(=[O:20])=[O:19].C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.O1CCOCC1>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:24]4[CH:25]=[CH:26][C:21]([S:18]([CH3:17])(=[O:20])=[O:19])=[CH:22][CH:23]=4)[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (200 mg, 0.85 mmol, 1.0 equiv.), 4-(methylsulfonyl)phenylboronic acid (187 mg, 0.93 mmol, 1.1 equiv.), Pcy3 (57 mg, 0.204 mmol, 0.24 equiv.), Pd2 (dpa)3 (78 mg, 0.085 mmol, 0.1 equiv.), K3PO4 (722 mg, 3.4 mmol, 4 equiv.), dioxane (5 ml) and water (1 ml) was added to the filtrate. The reaction mixture was heated to 100° C. for 15 h under nitrogen atmosphere. The residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 100:1) to afford title compound N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-(4-(methylsulfonyl)phenyl) pyrimidin-4-amine (Compound 15) (16.2 mg, 5.4%) as white solid. LC-MS (m/z)=356.0 [M+H]+; 1H NMR (300 MHz, DMSO-d6): δ 0.73 (m, 2H), 0.94 (m, 2H), 1.91 (m, 1H), 3.26 (s, 3H), 8.06 (d, J=8.7 Hz, 2H), 8.40 (d, J=6 Hz, 2H), 8.53 (d, J=8.4 Hz, 2H), 9.99 (s, 1H), 12.10 (s, 1H).

Workup

additionwas added to the filtrate
customThe residue was purified by silica gel chromatography (CH2Cl2/methanol 500:1 to 100:1)

Sources & evidence

ORD record: ord-219a498e85e240b48f1d3d0e9ba8292f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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