p-Toluenesulfonic acid → 2-(3-Acetamidophenylamino)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxamide

HRID 533477Notes

Reaction equation

CS([C:4]1[N:9]=[C:8]([NH:10][C:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12]2)[C:7]([C:20]([NH2:22])=[O:21])=[CH:6][N:5]=1)=O.[C:23]([NH:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=1)[NH2:30])(=[O:25])[CH3:24].CC1C=CC(S(O)(=O)=O)=CC=1>CN1C(=O)CCC1>[C:23]([NH:26][C:27]1[CH:28]=[C:29]([NH:30][C:4]2[N:9]=[C:8]([NH:10][C:11]3([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:13][CH2:12]3)[C:7]([C:20]([NH2:22])=[O:21])=[CH:6][N:5]=2)[CH:31]=[CH:32][CH:33]=1)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(methylsulfinyl)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxamide (50 mg, 0.16 mmol) in NMP (1 mL) was added 3-acetamidoaniline (27 mg, 0.18 mmol) and pTsOH*H2O (30 mg, 0.16 mmol). The mixture was heated at 100° C. for 2 h, cooled to room temperature, and purified by preparative HPLC to give 2-(3-acetamidophenylamino)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxamide (38 mg). MS found for C22H22N6O2 as (M+H)+ 403.5. λ=251.1.

Workup

temperaturecooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-e4f279e7341c450795023278280256d6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853230B2

Reaction notes

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