Sodium Bicarbonate → 3-[3-({4-[(3-Bromo-5-methoxybenzyl)amino]-5-chloropyrimidin-2-yl}amino)phenyl]propan-1-ol

HRID 1614975Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)[CH2:5][NH:6][C:7]1[C:12]([Cl:13])=[CH:11][N:10]=[C:9](Cl)[N:8]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][OH:30])[CH:24]=[CH:25][CH:26]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)[CH2:5][NH:6][C:7]1[C:12]([Cl:13])=[CH:11][N:10]=[C:9]([NH:20][C:21]2[CH:22]=[C:23]([CH2:27][CH2:28][CH2:29][OH:30])[CH:24]=[CH:25][CH:26]=2)[N:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Into a reaction flask were added N-(3-bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine (2.0 g, 5.5 mmol), 1,4-dioxane (30 mL), 3-(3-aminophenyl)propan-1-ol (1.2 g, 8.3 mmol, prepared according to Example 12, Step B), and p-toluenesulfonic acid monohydrate (0.12 g, 0.63 mmol). The mixture was heated at 70° C. over two days and NaHCO3 (saturated aqueous solution) was added. After removal of the organic solvent, the aqueous layer was extracted with methylene chloride twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated to give the desired product as a white powder (2.6 g, 99%). LCMS for C21H22BrClN4O2 (M+H)+: m/z=477.0, 479.0.

Workup

customAfter removal of the organic solvent
extractionthe aqueous layer was extracted with methylene chloride twice
washThe combined organic layers were washed with water and brine successively
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1c801ceecb9d4586859fbf77e2e7e425
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765727B2

Reaction notes

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