Dichloromethane → 5-Bromopyrimidine-2,4-diamine

HRID 1512091Notes

Reaction equation

HRID 1512091 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O.C(Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[Br:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 674312,4-Diaminopyrimidine

Product 1

HCID 234235905-Bromopyrimidine-2,4-diamineYield 81.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2,4-diaminopyrimidine (1.0 g, 9.1 mmol) in chloroform (30 mL) was added N-bromosuccinimide (1.62 g, 9.08 mmol). The solution was stirred in the dark for 12 hours, at which time it was added to CH2Cl2 (150 mL) and 1N NaOH (50 mL). The solid that formed was filtered, rinsed with water and concentrated in vacuo, yielding 1.4 g (74%) of 5-bromopyrimidine-2,4-diamine. LCMS (m/z): 189/191 (MH+). 1H NMR (DMSO-d6): δ 7.78 (s, 1H), 6.58 (bs, 2H), 6.08 (bs, 2H).

Workup

  1. customThe solid that formed
  2. filtrationwas filtered
  3. washrinsed with water
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f350ab94fd034d7a9e08987f014457a4
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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