2,5-Dichloro-N-(5-methyl-1H-pyrazol-3-yl)-4-pyrimidinamine → HCID 44611101, compound

HRID 1897704Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2,5-dichloro-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (120 mg, 0.49 mmol) and 2,5-dimethyl-4-(piperidin-2-yl)aniline (100 mg, 0.49 mmol) in 2-propanol (10 mL) was treated with conc. aqueous HCl (7 drops). The mixture was sealed and heated in a microwave at 130° C. for 45 min. The mixture was concentrated to afford 5-Chloro-N2-(2,5-dimethyl-4-(piperidin-2-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine; ESMS m/z 412.1 (M+H+). The crude product was used directly for the next step without further purification.

Workup

customThe mixture was sealed
concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-d02c0f70125944ccb86d99d9af1476d3
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519129B2

Reaction notes

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