Sodium methanethiolate → HCID 18507454, compound

HRID 1355862Notes

Reaction equation

HRID 1355862 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[C:5]([F:16])=[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)[N:3]=1.[CH3:22][S-:23].[Na+]>COCCOC>[F:16][C:5]1[C:4]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)=[N:3][C:2]([NH2:1])=[N:7][C:6]=1[S:23][CH3:22]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86583749HCID 86583749, compound

Product 1

HCID 18507454HCID 18507454, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A stirred solution of 260 mg (0.80 mmol) trifluoromethanesulfonic acid 2-amino-5-fluoro-6-furan-2-yl-pyrimidin-4-yl ester and 560 mg (7.99 mmol) sodium methanethiolate in 10 ml dry DME under argon was heated at 50° C. for 2 hours. The reaction mixture was then concentrated in vacuo. Flash chromatography (ethyl acetate/hexane 1/2) followed by trituration in ether/hexane afforded 65 mg (36%) 5-fluoro-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine as a white crystalline solid. EI-MS m/e (%): 225 (M+, 100), 180 (28).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-d5ebf6ba823140da84a799e27e7a76f1
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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