Lawesson's reagent → HCID 57818467, compound

HRID 705596Notes

Reaction equation

[F:1][C:2]1[C:3]([NH:17][C:18](=O)[CH3:19])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>ClCCCl>[F:1][C:2]1[C:3]([NH:17][C:18](=[S:30])[CH3:19])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-(5-fluoro-2-(4-fluorobenzyloxy)pyrimidin-4-yl)acetamide (50 mg, 0.42 mmol) was stirred in a Biotage Initiator® microwave vessel with 1,2-dichloroethane (3 mL) and Lawesson's reagent (170 mg, 0.42 mmol). The vessel was heated in a Biotage Initiator® microwave to 100° C. for 5 minutes then cooled room temperature, filtered, and diluted with CH2Cl2. The reaction mixture was then washed brine, and the layers were separated. The organic extract was dried onto silica and purified by flash chromatography. The product-containing fractions were then evaporated to dryness and purified again by reverse-phase HPLC to give 4 mg of N-(5-fluoro-2-(4-fluorobenzyl-oxy)pyrimidin-4-yl)ethanethioamide (4%) as a yellow glass: 1H NMR (CDCl3) δ 9.34 (b, 1H), 8.29 (d, J=3 Hz, 1H), 7.41 (m, 2H), 7.06 (m, 2H), 5.33 (s, 2H), 3.13 (s, 3H); HPLC-MS (ESI): m/z 294 (ES−).

Workup

temperaturethen cooled room temperature
filtrationfiltered
additiondiluted with CH2Cl2
customwashed brine, and the layers were separated
extractionThe organic extract
customwas dried onto silica
custompurified by flash chromatography
customThe product-containing fractions were then evaporated to dryness
custompurified again by reverse-phase HPLC

Sources & evidence

ORD record: ord-7b1150089f0541f993dbeed39e52c6d4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174970B2

Reaction notes

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