Ammonia → HCID 5329597, compound

HRID 1838959Notes

Reaction equation

HRID 1838959 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]([N:16]=O)=[C:4]([NH2:18])[N:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].N>O>[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]([NH2:18])[N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24489Sodium DithioniteHCID 3981486-(Cyclohexylmethoxy)-5-nitrosopyrimidine-2,4-diamine

Product 1

HCID 5329597HCID 5329597, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a strirred suspension of 2,6-diamino-5-nitroso-4-cyclohexylmethoxypyrimidine (0.10 g, 0.4 mmol) in water (5 ml) at 50° C. was added sodium dithionite (0.16 g, 0.92 mmol) in portions over a period of 5 h. The reaction mixture was allowed to cool to room temperature and stirred at ambient temperature overnight. The pH of the solution was adjusted to 7 with aqueous ammonia solution (2 ml), and the resulting fine yellow precipitate was collected by filtration and washed with water. The product was purified by recrystallisation from water (0.06 9, 60%), m.p. 154° C.; (Found: C, 55.50; H, 7.95; N, 29.34% C11H19N5O requires C, 55.69; H, 8.02; N, 29.53%); δH (200 MHz, d6-DMSO) 1.02-1.39 (5H, m, C6H11), 1.71-1.89 (6H, m, C6H11), 3.22 (2H, br s, NH2), 4.03 (2H, d, OCH2, J=6.53 Hz), 5.32 (2H, br s, NH2), 5.71 (2H, br s, NH2); m/z (+EI) 237 (M+, 84%), 155 (MH+-C7H13, 100), 124 (MH+-C7H13O, 15).

Workup

  1. filtrationthe resulting fine yellow precipitate was collected by filtration
  2. washwashed with water
  3. customThe product was purified by recrystallisation from water (0.06 9, 60%), m.p. 154° C.

Sources & evidence

ORD record
ord-727d461a0b424fb7b2ab6619f905263a
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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