N-bromobutanimide → HCID 118036259, compound

HRID 1777921Notes

Reaction equation

HRID 1777921 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[N:8]=2)[CH2:2]1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)Cl>[Br:21][C:12]1[C:7]([O:6][C@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[N:8][C:9]([NH2:13])=[N:10][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 118036167HCID 118036167, compound2×

Product 1

HCID 118036259HCID 118036259, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

(S)-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-amine (intermediate 62, 33 mg, 0.182 mmol) was dissolved in DCM (4 ml), treated with NBS (35.7 mg, 0.200 mmol) and stirred at 25° C. for 1 h. The reaction solution was diluted in DCM and washed with NaOH (1 M in water) and brine. The organic layer was dried over Na2SO4, filtered and concentrated under vacuum to obtain the title compound as a white solid. (UPLC-MS 3) tR 0.67 min; ESI-MS 260.1, 262.0 [M+H]+.

Workup

  1. washwashed with NaOH (1 M in water) and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9e5b920107c449fdb72581f0cea7f328
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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