Potassium Phosphate, Tribasic → HCID 58169438, compound

HRID 1484861Notes

Reaction equation

[Si:1]([O:8][CH2:9][C:10]1[C:11]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:25][CH2:24]3)[NH:20][N:19]=2)=[N:12][C:13](Cl)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:1]([O:8][CH2:9][C:10]1[C:11]([NH:17][C:18]2[CH:22]=[C:21]([CH:23]3[CH2:25][CH2:24]3)[NH:20][N:19]=2)=[N:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-((tert-butyldimethylsilyloxy)methyl)-2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amine (200 mg, 0.53 mmol, 1.0 eq), phenylboronic acid (90.5 mg, 0.742 mmol, 1.4 eq), Pd2(dba)3 (48.5 mg, 0.053 mmol, 0.1 equiv.), tricyclohexylphosphine (35.7 mg, 0.127 mmol, 0.24 equiv.), K3PO4 (450 mg, 2.12 mmol, 4 eq) in 1,4-dioxane (20 mL) and water (4 mL) was stirred at 100° C. under a nitrogen atmosphere for 15 h. The reaction mixture was allowed to cool to room temperature and concentrated to give a residue, which was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 100:1 as eluent) to afford 5-((tert-butyldimethylsilyloxy)methyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidin-4-amine (50 mg, 22.5%) as a solid. LC-MS (m/z)=422.2 [M+H]+.

Workup

temperatureto cool to room temperature
concentrationconcentrated
customto give a residue, which
customwas purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 100:1 as eluent)

Sources & evidence

ORD record: ord-f951c8a80b2a4979828f8bb58b53e5c2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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