N-bromobutanimide → HCID 11201291, compound

HRID 254176Notes

Reaction equation

HRID 254176 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.[Br: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]([Br: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 67184N-bromobutanimideHCID 59022902HCID 59022902, compound

Product 1

HCID 11201291HCID 11201291, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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-bromosuccinimide (28 mg, 0.156 mmol), stirred for 2 h, 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 (50 mg, 82%) as a beige solid.

Workup

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

Sources & evidence

ORD record
ord-9e4197acc6ef4d75986563d2683df8b5
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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