Ammonia → HCID 23071590, compound

HRID 905700Notes

Reaction equation

CS([C:4]1[C:9]([C:10]([NH2:12])=[O:11])=[CH:8][N:7]=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N+:21]3([O-])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:16][CH:15]=2)[N:5]=1)=O.[CH:28]1([NH2:31])[CH2:30][CH2:29]1.C(N(C(C)C)CC)(C)C.S([O-])(O)=O.[Na+].N>C(Cl)(Cl)Cl>[CH:28]1([NH:31][C:4]2[C:9]([C:10]([NH2:12])=[O:11])=[CH:8][N:7]=[C:6]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[CH:16][CH:15]=3)[N:5]=2)[CH2:30][CH2:29]1

Participants

Conditions

Temperature: 90 °C

Procedure

A 1 ml portion of chloroform solution containing 11.7 mg of 4-methylsulfinyl-2-({4-[(N-oxidomorpholin-4-yl)methyl]phenyl}amino)pyrimidine-5-carboxamide was mixed with 5.1 mg of cyclopropylamine and 5.8 mg of diisopropylethylamine, followed by stirring at 90° C. for 15 hours. A 1 ml portion of aqueous solution containing 50 mg of sodium hydrogen sulfite was added to the reaction mixture, followed by stirring at room temperature for 4 hours. This was mixed with 0.1 ml of aqueous ammonia and extracted with 2 ml of chloroform. By evaporating the solvent under a reduced pressure and fractionating the residue by an HPLC (Wakosil-II 5C18AR, 0.1% HCOOH—H2O/MeOH=7/3-0/10), 2.6 mg of 4-cyclopropylamino-2-(4-morpholin-4-ylmethylphenylamino)-pyrimidine-5-carboxamide was obtained.

Workup

additionwas added to the reaction mixture
stirringby stirring at room temperature for 4 hours
extractionextracted with 2 ml of chloroform
customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record: ord-3c8f47790b124eee9651f8a7fa6e72d6
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012959B2

Reaction notes

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