Triethylamine → [4-[6-(Aminomethyl)-2-methyl-pyrimidin-4-yl]oxyphenyl]methanesulfonamide

HRID 1520105Notes

Reaction equation

C(N(CC)CC)C.[C:8]([C:10]1[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][S:25]([NH2:28])(=[O:27])=[O:26])=[CH:20][CH:19]=2)[CH:11]=1)#[N:9].[H][H]>O1CCOCC1.CCO.[Pd]>[NH2:9][CH2:8][C:10]1[N:15]=[C:14]([CH3:16])[N:13]=[C:12]([O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][S:25]([NH2:28])(=[O:27])=[O:26])=[CH:22][CH:23]=2)[CH:11]=1

Participants

Conditions

Temperature: 22 °C

Procedure

Combine triethylamine (117.83 mL) and palladium 10% on charcoal (20.10 g) to a solution of [4-(6-cyano-2-methyl-pyrimidin-4-yl)oxyphenyl]methanesulfonamide (67 g, 211.35 mmoles) in a mixture of 1,4-dioxane (469 mL) and EtOH (201 mL; 159.05 g) in a PARR reactor. Maintain the mixture at 22° C. Seal the reactor and pressurize it with hydrogen (400 PSI). Shake the reactor for 18 h while maintaining it at 22° C. Thereafter open the reactor and filter of the solids. Rinse the solid residue with MeOH (1 L), a mixture of dioxane/MeOH 1:1 (1 L), and MeOH (3×1 L). Collect and concentrate the filtrate to provide a solid, Collect and dry the solid in a vacuum oven, (45° C., 15 mbar) to provide the title compound as yellow solid, 62.41 g, 77% yield. MS (m/z): 309 (M+1).

Workup

customSeal the reactor
temperatureShake the reactor for 18 h while maintaining it at 22° C
filtrationThereafter open the reactor and filter of the solids
washRinse the solid residue with MeOH (1 L)
additiona mixture of dioxane/MeOH 1:1 (1 L), and MeOH (3×1 L)
customCollect
concentrationconcentrate the filtrate
customto provide a solid
customCollect
customdry the solid in a vacuum oven, (45° C., 15 mbar)

Sources & evidence

ORD record: ord-7e2dc601304d4811a8a7066620a159eb
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073901B2

Reaction notes

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