HCID 10130617, compound → 2,4-Pyrimidinediamine, 5-nitroso-6-(phenylmethoxy)-

HRID 1838961Notes

Reaction equation

HRID 1838961 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([NH2:16])[N:3]=1.[N:17]([O-])=[O:18].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([N:17]=[O:18])=[C:4]([NH2:16])[N:3]=1

Participants

5

Reactant 2

HCID 10130617HCID 10130617, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 1810292,4-Pyrimidinediamine, 5-nitroso-6-(phenylmethoxy)-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2,6-Diamino-4-benzyloxypyrimidine (0.5 g, 2.3 mmol) was dissolved in warm acetic acid (30%, 10 ml) and the reaction mixture was heated to 80° C. A solution of sodium nitrite (0.22 g, 3.19 mmol) in water (5 ml) was added dropwise over 1 h, when an excess of oxidant was evident by starch-iodide paper. The reaction mixture was allowed to cool to room temperature, and the violet crystals which deposited were collected and washed with water (0.53 g, 98%), m.p. decomposed 209° C.; (Found: C, 55.32; H, 5.28; N, 26.47% C11H11N5O2 0.1 H2O C, 55.98; H, 4.75; N, 29.69%); νmax/cm−1 3408 (NH), 2952 (CH2), 1610 (C6H5), 1518 (NO); δH (200 MHz, d6-DMSO) 5.69 (2H, s, OCH2), 7.44-7.68 (5H, m, C6H5), 8.0 (2H, d, NH2), 8.17 (1H, s, NH) , 10.19 (1H, s, NH); m/z (+EI) 245 (M+, 25%), 91 (100), 65 (9).

Workup

  1. temperatureto cool to room temperature
  2. customthe violet crystals which deposited were collected
  3. washwashed with water (0.53 g, 98%)
  4. customm.p. decomposed 209° C.

Sources & evidence

ORD record
ord-6cb7339ad3d24e178d4fad5c5532e0b5
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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