Chlorosuccinimide → HCID 118036713, compound

HRID 1777918Notes

Reaction equation

HRID 1777918 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([Cl:21])C(=O)C1>C(#N)C.C(Cl)Cl>[Cl: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

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 118036167HCID 118036167, compound2×

Product 1

HCID 118036713HCID 118036713, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (S)-4-((tetrahydrofuran-3-yl)oxy)pyrimidin-2-amine (intermediate 62, 100 mg, 0.552 mmol) in acetonitrile (4 ml) was treated with NCS (100 mg, 0.749 mmol) and stirred at 25° C. for 24 h. Then, the mixture was heated at 80° C. for 3 h. The resulting solution was cooled to room temperature, diluted with DCM and washed with NaOH (1 M in water) and brine. The org layer was dried over Na2SO4, filtered and concentrated. The crude was purified by normal phase chromatography (12 g gold silica gel cartridge, heptanes/EtOAc 100:0 to 8:92) to give the title compound as a white solid. (UPLC-MS 3) tR 0.64 min; ESI-MS 216.1 [M+H]+.

Workup

  1. temperatureThen, the mixture was heated at 80° C. for 3 h
  2. temperatureThe resulting solution was cooled to room temperature
  3. washwashed with NaOH (1 M in water) and brine
  4. dry with materialThe org layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified by normal phase chromatography (12 g gold silica gel cartridge, heptanes/EtOAc 100:0 to 8:92)

Sources & evidence

ORD record
ord-acbbc1a65b4d49a3969c4d5fe5f55134
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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