Bicarbonate Ion → 6-(Benzylamino-methyl)-2,4-pteridinediamine

HRID 1272483Notes

Reaction equation

HRID 1272483 reaction equation
Br.Br[CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-]>CN(C)C(=O)C>[CH2:16]([NH:23][CH2:3][C:4]1[N:5]=[C:6]2[C:11](=[N:12][CH:13]=1)[N:10]=[C:9]([NH2:14])[N:8]=[C:7]2[NH2:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 769Bicarbonate IonHCID 7504BenzylamineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Product 1

HCID 184557476-(Benzylamino-methyl)-2,4-pteridinediamineYield 62%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-bromomethyl-2,4-pteridinediamine hydrobromide (35.7 mg, 0.106 mmol) in anhydrous N,N dimethylacetamide was added benzylamine (28.6 ul, 0.212 mmol). The reaction mixture was stirred at 50° C. overnight. The crude product was poured into saturated bicarbonate solution. The resulted precipitate was collected and purified by preparative HPLC. 17.7 mg product was obtained. Yield: 62%; 1H NMR (500 MHz, DMSO-d6): δ 4.30499(s, 2H), 4.51599(s, 2H), 7.42787–7.47298(m, 3H), 7.50007–7.51927 (m, 2H), 8.87751(s, 1H); ESI-MS: m/z 282 (M++1)

Workup

  1. customThe resulted precipitate was collected
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9c0e5e93276546f39777a4f3fceafa60
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

Loading…