Hydrochloric Acid → N-[2-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]phenyl]ethyl]acetamide

HRID 1679127Notes

Reaction equation

HRID 1679127 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.Cl.[OH-].[Na+].Br.[NH2:18][C:19]1[N:28]=[C:27]([NH2:29])[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH2:30]Br)[N:25]=2)[N:20]=1>CC(N(C)C)=O>[NH2:18][C:19]1[N:28]=[C:27]([NH2:29])[C:26]2[C:21](=[N:22][CH:23]=[C:24]([CH2:30][NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:6][CH:7]=3)[N:25]=2)[N:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 314928N-[2-(4-aminophenyl)ethyl]acetamideHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Product 1

HCID 428480N-[2-[4-[[(2,4-diamino-6-pteridinyl)methyl]amino]phenyl]ethyl]acetamideYield 70%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of N-[2-(4-aminophenyl)ethyl]acetamide (713 mg, 4 mmoles) and I (672 mg, 2 mmoles) in DMAC (8 ml) was stirred under N2 at about 25° in a stoppered flask protected from light for 2 days. The precipitate was isolated by filtration and the solid on the funnel was washed with DMAC (2 × 4 ml). The filtrate was set aside, and the solid was then washed with EtOH (5 ml) and H2O (2 × 3 ml). The addition of an equal volume of H2O to the DMAC filtrate afforded more product which was isolated by filtration and washed with H2O. Evaporation of the EtOH-H2O washes also afforded more product, which was triturated with Et2O and isolated by filtration. The combined yield was 70% (609 mg). A sample obtained in this manner was recrystallized from MeOH to give the pure product in about 50% recovery. Anal. Calcd for C17H20N8O.HBr.2H2O: C, 43.50; H, 5.37; N, 23.88. Found: C, 43 .40; H, 5.42; N, 23.82. Spectral data: λ max, nm (ε × 10-3), 0.1 N HCl, 246 (17.9), 292 (5.80), 337 (10.2), 347 (sh); pH 7, 257 (27.6), 280 (sh), 372 (7.70); 0.1 N NaOH, 257 (28.6), 280 (sh), 372 (7.96); pmr (DMSO-d6), δ 1.76 (s, 3, CH3), 2.56 (m, 2, C6H4 --CH 2 CH2), 3.16 (m, 2, CH2NHCO), 4.52 (s, 2, CH2NHC6H4), 6.80 (m, 4, C6H4), 8.84 (s, 1, C7 --H).

Workup

  1. customThe precipitate was isolated by filtration
  2. washthe solid on the funnel was washed with DMAC (2 × 4 ml)
  3. washthe solid was then washed with EtOH (5 ml) and H2O (2 × 3 ml)
  4. additionThe addition of an equal volume of H2O to the DMAC filtrate
  5. customafforded more product which
  6. customwas isolated by filtration
  7. washwashed with H2O
  8. customEvaporation of the EtOH-H2O
  9. customalso afforded more product, which
  10. customwas triturated with Et2O
  11. customisolated by filtration
  12. customA sample obtained in this manner
  13. customwas recrystallized from MeOH
  14. customto give the pure product in about 50% recovery

Sources & evidence

ORD record
ord-0f09bb24f8c84d1c8ab0f1001d3e0ac3
Source dataset
uspto-grants-1978_03
Patent number
US04079056

Reaction notes

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