HCID 71437378, compound → 6-Bromomethyl-2,4-pteridinediamine

HRID 1432129Notes

Reaction equation

HRID 1432129 reaction equation
[Br-].[Br-].[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([NH2:11])=[C:6]([NH2:12])[N:5]=1.[Br:13][CH2:14][C:15](=O)[CH:16]=NO>CO>[NH2:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]2[C:6](=[N:12][CH:16]=[C:15]([CH2:14][Br:13])[N:11]=2)[N:5]=1

Participants

4

Reactant 2

HCID 71437378HCID 71437378, compoundHCID 131726730HCID 131726730, compound

Product 1

HCID 4293426-Bromomethyl-2,4-pteridinediamineYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A suspension of 5 mmol 2,4,5,6-tetraminopyrimidine dibromide in 50 ml methanol was treated with a solution of 7.5 mmol β-bromopyruvaldoxime in 10 ml of methanol at reflux temperature for 2 h. The 2,4-diamino-6-(bromomethyl)pteridine was collected after neutralization with concentrated NH3 at room temperature, washed with methanol, ether and dried at 100° C. in an oven. 1H NMR (250 MHz, ppm, DMSO-d6), δ 8.84 (s, 1H, C7—H). The yield was 88%.

Workup

  1. temperatureat reflux temperature for 2 h
  2. customThe 2,4-diamino-6-(bromomethyl)pteridine was collected after neutralization with concentrated NH3 at room temperature
  3. washwashed with methanol, ether
  4. customdried at 100° C. in an oven

Sources & evidence

ORD record
ord-387672240cb0412c9460e3ed815f0555
Source dataset
uspto-grants-2009_11
Patent number
US07612071B2

Reaction notes

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