Lawesson's reagent → 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carbothioamide

HRID 1484992Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:11][C:12]2[CH:16]=[C:15]([CH:17]3[CH2:19][CH2:18]3)[NH:14][N:13]=2)=[N:4][C:5]([C:8]([NH2:10])=O)=[N:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1(C)C=CC=CC=1.C1COCC1>[Cl:1][C:2]1[C:3]([NH:11][C:12]2[CH:16]=[C:15]([CH:17]3[CH2:19][CH2:18]3)[NH:14][N:13]=2)=[N:4][C:5]([C:8](=[S:29])[NH2:10])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carboxamide (500 mg, 1.79 mmol) and Lawesson's reagent (1.45 g, 3.58 mmol, 2.0 eq) in toluene (30 ml) and THF (20 ml) was stirred at 50° C. for 17 h, and then, concentrated. The residue was recrystallized with toluene to give the crude 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carbothioamide (2.3 g, directly used for the next step). LC-MS (m/z)=295.0 [M+H]+.

Workup

concentrationconcentrated
customThe residue was recrystallized with toluene

Sources & evidence

ORD record: ord-76a7709ff11b46ef97ff8da2b2b38c56
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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