Sodium Iodide → HCID 178428184, compound

HRID 383800Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH:10]1([C:13]2[CH:17]=[C:16]([NH2:18])[NH:15][N:14]=2)[CH2:12][CH2:11]1.[Na+].[I-].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:18][C:16]2[NH:15][N:14]=[C:13]([CH:10]3[CH2:12][CH2:11]3)[CH:17]=2)[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the solution of 2,4-dichloro-6-methylpyrimidine (1.63 g) and 3-cyclopropyl-1H-pyrazol-5-amine (1.24 g) in DMF (20 ml) was added NaI (1.49 g) and DIEA (1.72 ml). And the mixture was stirred at 80° C. overnight. The mixture was concentrated to remove DMF. The residue was suspended into EtOAc. The insoluble material was filtered off and washed with EtOAc. The filtrate was concentrated and the residue was pufiried with silica gel column chromatography (eluent: CHCl3/MeOH=98/2˜90/10) to give 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-6-methylpyrimidin-4-amine (1054 mg) as a pale pink solid.

Workup

concentrationThe mixture was concentrated
customto remove DMF
filtrationThe insoluble material was filtered off
washwashed with EtOAc
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-fcdff161da3b4da2b4af59f44a446628
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367690B2

Reaction notes

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