Cyanogen Bromide → HCID 178493710, compound

HRID 629003Notes

Reaction equation

HRID 629003 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:5][C:6]([C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)=[N:7][CH:8]=1.[N:23]#[C:24]Br>C(#N)C.O>[CH3:1][O:2][C:3]1[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]3[NH:15][C:24]([NH2:23])=[N:16][C:11]=3[CH:10]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 67297289HCID 67297289, compound

Product 1

HCID 178493710HCID 178493710, compoundYield 51.78%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 4-(5-methoxy-4-morpholin-4-yl-pyrimidin-2-yl)-benzene-1,2-diamine (0.58 g, 1.0 eq.) and ACN/H2O (5 ml/1 ml). In ice bath, cyanogen bromide (0.3 g, 1.5 eq) was added to mixture solution dropwisely. The solution was stirred overnight at room temperature, quenched with a NaHCO3(sat.) solution, and then filtered to give a light brown solid (0.32 g, 51.78%), which was dried in vacuo to give a product.

Workup

  1. customquenched with a NaHCO3(sat.) solution
  2. filtrationfiltered

Sources & evidence

ORD record
ord-43d0f6f83c094289b97c0e337feacb9e
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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