Chlorosuccinimide → HCID 59022944, compound

HRID 254175Notes

Reaction equation

HRID 254175 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH3:20])[N:13]=2)=[O:9])[CH:5]=[C:4]([C:21]2[O:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[N:3]=1.[Cl:27]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH3:20])[N:13]=2)=[O:9])[C:5]([Cl:27])=[C:4]([C:21]2[O:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[N:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 59022902HCID 59022902, compound

Product 1

HCID 59022944HCID 59022944, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-amino-N-(6-methoxymethyl-2-pyridylmethyl)-6-(5-methyl-2-furyl)pyrimidine-4-carboxamide (50 mg, 0.142 mmol) in acetic acid (10 mL) at room temperature was treated with N-chlorosuccinimide (24 mg, 0.156 mmol), stirred at 100° C. for 2 h, cooled to room temperature, concentrated in vacuo and partitioned between EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL). The organic phase was dried (MgSO4), concentrated in vacuo and the resulting solid was triturated with diethyl ether and filtered to give the title compound (30 mg, 54%) as a beige solid.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. custompartitioned between EtOAc (20 mL) and saturated aqueous NaHCO3 (20 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customthe resulting solid was triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d29fc24343e744f0824f2962ed073cb0
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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