Water → HCID 18365137, compound

HRID 380450Notes

Reaction equation

HRID 380450 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]([NH2:16])=[C:4]([NH2:17])[N:3]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=[O:19].O>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:5]2[C:4]([N:3]=1)=[N:17][C:18](=[O:19])[N:16]=2

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 5329597HCID 5329597, compound

Product 1

HCID 18365137HCID 18365137, compoundYield 58.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,5,6-triamino-4-cyclohexylmethyloxypyrimidine (1.0 g, 4.24 mmol) and 1,1′-carbonyldiimidazole (0.69 g, 4.24 mmol) in anhydrous DMF (5 ml) was stirred under nitrogen at ambient temperature for 48 h. Addition of water (100 ml) afforded a white solid which was collected by filtration, redissolved in 2 M sodium hydroxide solution (200 ml), and filtered. The filtrate was neutralised with glacial acetic acid and allowed to stand at 4° C. for 2 h, when the precipitate which deposited was collected and washed thoroughly with water. Recrystallisation from aqueous ethanol yielded the required product (0.65 g, 58%), m.p. 297° C.; (Found: C. 54.66; H, 6.47;. N, 26.63% C12 H17 N5O2 requires C, 54.75; H, 6.46; N, 26.62%); δH (200 MHz, d6-DMSO) 1.04-1.39 (δH, m, C6H11), 1.76-1.90 (6H, m, C6H11), 4.17 (2H, OCH2, J=6.53 Hz), 6.15 (2H. br s, NH2), 10.49 (1H, br s, NH), 1 1.09 (1H, br s, NH); m/z (+EI) 263 (M+, 75%), 167 (MH+—C7H13, 100), 81 (6), 69 (7).

Workup

  1. customafforded a white solid which
  2. filtrationwas collected by filtration
  3. dissolutionredissolved in 2 M sodium hydroxide solution (200 ml)
  4. filtrationfiltered
  5. customwhen the precipitate which deposited was collected
  6. washwashed thoroughly with water
  7. customRecrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-f05cda6bf459492f95852203548f8b69
Source dataset
uspto-grants-2001_10
Patent number
US06303618B1

Reaction notes

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