N-Bromosuccinamide → HCID 178433367, compound

HRID 472212Notes

Reaction equation

HRID 472212 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[CH:5]=[C:4]([CH3:16])[N:3]=1.[Br:17]NC(=O)CCC(N)=O>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)[C:5]([Br:17])=[C:4]([CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 178428544HCID 178428544, compound

Product 1

HCID 178433367HCID 178433367, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (trans-4-(2-amino-6-methylpyrimidin-4-ylamino)cyclohexanol (1.33 g, 5.98 mmol) in chloroform (15 mL) was added N-bromosuccinamide (1.08 g, 6.04 mmol). After stirring at room temperature for 1.5 hr, the solution was concentrated. The residue was purified by flash chromatography eluting with chloroform/7 N ammonia in methanol (0.5-5%) to afford the title compound (1.14 g, 63%).

Workup

  1. concentrationthe solution was concentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with chloroform/7 N ammonia in methanol (0.5-5%)

Sources & evidence

ORD record
ord-f5723e81a1dd4ff0bc284025011c6572
Source dataset
uspto-grants-2014_01
Patent number
US08633204B2

Reaction notes

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