Acetyl chloride → N-[5-fluoro-2-(thiophen-2-ylmethoxy)pyrimidin-4-yl]acetamide

HRID 705561Notes

Reaction equation

HRID 705561 reaction equation
[F:1][C:2]1[C:3]([NH2:15])=[N:4][C:5]([O:8][CH2:9][C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.[C:16](Cl)(=[O:18])[CH3:17].CN1CCOCC1>C(Cl)Cl>[F:1][C:2]1[C:3]([NH:15][C:16](=[O:18])[CH3:17])=[N:4][C:5]([O:8][CH2:9][C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 79724-Methylmorpholine2×HCID 578186595-Fluoro-2-(thiophen-2-ylmethoxy)pyrimidin-4-ylamine

Product 1

HCID 57818818N-[5-fluoro-2-(thiophen-2-ylmethoxy)pyrimidin-4-yl]acetamideYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 2 dram screw cap vial, a solution of 5-fluoro-2-(thiophen-2-ylmethoxy)-pyrimidin-4-ylamine (0.10 g, 0.4 mmol) in CH2Cl2 was treated with acetyl chloride (0.032 g, 0.4 mmol,) and PS-NMM (0.42 g, 0.8 mmol), a resin-bound equivalent of N-methyl morpholine (NMM). The mixture was shaken at RT for 12 h. The reaction mixture was filtered and the solvent evaporated to yield 0.084 g (75%) of the title compound as white solid: mp 134-136° C.; 1H NMR (300 MHz, CDCl3) δ 8.24 (d, J=2.6 Hz, 1H), 7.86 (bs, 1H), 7.31 (m, 1H), 7.23 (m, 1H), 7.00 (m, 1H), 5.54 (s, 2H), 2.58 (s, 3H); MS (ESI) m/z 268 (M+H)+.

Workup

  1. customIn a 2 dram screw cap vial
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-c5ffeb4938264e91bc6dd5ccd19d62d7
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

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