m-Aminoacetanilide → 2-(3-acetamidophenylamino)-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxamide

HRID 384279Notes

Reaction equation

N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[C:14]([C:25]([NH2:27])=[O:26])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[C:28]([NH:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35])(=[O:30])[CH3:29].CC1C=CC(S(O)(=O)=O)=CC=1.O>CN1C(=O)CCC1>[C:28]([NH:31][C:32]1[CH:33]=[C:34]([NH:35][C:11]2[N:16]=[C:15]([NH:17][CH2:18][C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[C:14]([C:25]([NH2:27])=[O:26])=[CH:13][N:12]=2)[CH:36]=[CH:37][CH:38]=1)(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxamide (51 mg, 0.14 mmol) in NMP (0.8 mL) was added 3-acetamidoaniline (24 mg, 0.16 mmol) and pTsOH.H2O (27 mg, 0.14 mmol). The mixture was heated at 100° C. for 2 h, cooled to room temperature, purified by preparative HPLC to give 2-(3-acetamidophenylamino)-4-((1-methyl-1H-pyrazol-4-yl)methylamino)pyrimidine-5-carboxamide (40 mg). MS found for C18H20N8O2 as (M+H)| 381.5. λ=242.8.

Workup

temperaturecooled to room temperature
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-245a299153ff446e88d8e494af01a726
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367689B2

Reaction notes

Loading…