Water → HCID 10422576, compound

HRID 260045Notes

Reaction equation

HRID 260045 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.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].O>CN(C)C=O>[CH:15]1[CH:14]=[CH:13][C:12]([CH2:11][O:10][C:4]2[C:5]3[NH:9][C:18]([NH:8][C:6]=3[N:7]=[C:2]([NH2:1])[N:3]=2)=[O:19])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 98160442,5,6-Triamino-4-Benzyloxypyrimidine

Product 1

HCID 10422576HCID 10422576, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4,5-Triamino-6-benzyloxypyrimidine (Pfleiderer et al., Chem. Ber., 94, 12-18 (1961)) (1.85 g, 8 mmol) and 1,1'-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 2N 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) λmax 243 nm (ε=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 δ5.41 (s, 2H, ArCH2), 6.13 (s, 2H, NH2 , exchange with D2O), 7.33-7.51 (m, 5H, ArH), 10.46 (s, 1H, exchanges with D2O), 11.04 (s, 1H, exchanges with D2O); MS (EI) Calcd. m/z for C12H11N5O2 : 257.0912. Found: 257.0914. Anal. (C12H11N5O2. 1/2H2O) C, N, H.

Workup

  1. customto precipitate a white solid
  2. filtrationThe solid was collected by filtration
  3. dissolutiondissolved in 250 mL of aqueous 2N 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-60bb3a325d2d40c0a2e351d8dd9cdba6
Source dataset
uspto-grants-1996_06
Patent number
US05525606

Reaction notes

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