Benzene → 6-Bromomethyl-2,4-pteridinediamine

HRID 1272479Notes

Reaction equation

HRID 1272479 reaction equation
[Br:1]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C(=O)C.Br.[NH2:29][C:30]1[N:39]=[C:38]([NH2:40])[C:37]2[C:32](=[N:33][CH:34]=[C:35]([CH2:41]O)[N:36]=2)[N:31]=1.C1C=CC=CC=1>CCOCC>[Br:1][CH2:41][C:35]1[N:36]=[C:37]2[C:32](=[N:33][CH:34]=1)[N:31]=[C:30]([NH2:29])[N:39]=[C:38]2[NH2:40]

Participants

6

Reactant 4

HCID 241Benzene2×HCID 31374DimethylacetamideHCID 70579Triphenylphosphine dibromideHCID 2773879(4-Amino-2-imino-2,3-dihydropteridin-6-yl)methanol--hydrogen bromide (1/1)

Product 1

HCID 4293426-Bromomethyl-2,4-pteridinediamineYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the solution of dibromotriphenylphosphine (2.4337 g, 5.76 mmol) of 2 ml anhydrous N,N-dimethylacetamide was added (2,4-Diamino-Pteridin-6-yl)-methanol hydrobromide (335.8 mg, 1.747 mmol). The mixture is the stirred at RT for overnight. The solution was treated with benzene. The filtered solid was then successively treated with benzene and ether and evaporate the remaining solid. The residue was dissolved in minimum 48% HBr at RT which then was added MeCN to give a tan solid precipitate. Collect the solid in ice water bath and wash it with MeCN and ether. 352 mg product was obtained. Yield 60%; 1H NMR (500 MHz, DMSO-d6): δ 4.86021(s, 2H), 9.01 (s, 1H), 9.15 (s, 2H), 9.22 (s, 2H); ESI-MS: 255, 257(M++1)

Workup

  1. customevaporate the remaining solid
  2. dissolutionThe residue was dissolved in minimum 48% HBr at RT which
  3. additionthen was added MeCN
  4. customto give a tan solid precipitate
  5. customCollect the solid in ice water bath
  6. washwash it with MeCN and ether

Sources & evidence

ORD record
ord-c5473898f1964ee9919f99eecbc904e3
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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