Water → HCID 10422576, compound

HRID 619215Notes

Reaction equation

HRID 619215 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.O.CN(C)[CH:21]=[O:22]>>[CH:15]1[CH:14]=[CH:13][C:12]([CH2:11][O:10][C:4]2[C:5]3[NH:9][C:21]([NH:8][C:6]=3[N:7]=[C:2]([NH2:1])[N:3]=2)=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 98160442,5,6-Triamino-4-Benzyloxypyrimidine

Product 1

HCID 10422576HCID 10422576, compound

Procedure

2,4,5-Triamino-6-benzyloxypyrimidine (Pfleiderer et al., Chem. Ber., 94, 12-18 (1961)) (1.85 g, 8 mmol) and 1,11-carbonyldiimidazole (1.30 g, 8 mmol) were dissolved in anhydrous N,N-dimethylformamide (5 mL) under argon. The solution was stirred at room temperature overnight and was mixed with water (200 mL) to precipitate a white solid. The solid was collected by filtration, and dissolved in 250 mL of aqueous 2 N NaOH solution. Undissolved material was removed by filtration, and the filtrate was neutralized with glacial acetic acid to precipitate a white solid. The solid was collected by filtration, was washed with water, and was recrystallized from 50% aqueous ethanol to afford analytically pure 1c: yield, 1.63 g (79%); mp 256-257° C. dec.; UV (pH 1) 1max 243 nm (e=0.717×104), 306 (1.499×104); (pH 6.9) 243 (0.915×104), 290 (1.108×104); (pH 13) 249 (sh) (0.443×104), 293 (1.368×104); 1H NMR d 5.41 (s, 2 H, ArCH2), 6.13 (s, 2 H, NH2, exchange with D2O), 7.33-7.51 (m, 5 H, ArH), 10.46 (s, 1 H, exchanges with D2O), 11.04 (s, 1 H, exchanges with D2O); MS (EI) Calcd. m/z for C12H11N5O2 : 257.0912. Found: 257.0914. Anal. (C12H11N5O2. 1/2 H2O) C, N, H.

Workup

  1. customto precipitate a white solid
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved in 250 mL of aqueous 2 N NaOH solution
  4. customwas removed by filtration
  5. customto precipitate a white solid
  6. filtrationThe solid was collected by filtration
  7. washwas washed with water
  8. customwas recrystallized from 50% aqueous ethanol

Sources & evidence

ORD record
ord-cfc4278e518c41bda551083239f61d85
Source dataset
uspto-grants-1999_09
Patent number
US05958932

Reaction notes

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