HCID 5329584, compound → HCID 5329583, compound

HRID 1838963Notes

Reaction equation

HRID 1838963 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11]2)[CH:5]=[C:4]([NH2:16])[N:3]=1.[N:17]([O-])=[O:18].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11]2)[C:5]([N:17]=[O:18])=[C:4]([NH2:16])[N:3]=1

Participants

4

Reactant 2

HCID 5329584HCID 5329584, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 5329583HCID 5329583, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2,6-diamino-4-cyclohex-3-enylmethyloxypyrimidine (0.5 g, 2.27 mmol) in 30% acetic acid solution was heated to 80° C., and sodium nitrite solution (0.22 g, 3.19 mmol, in 10 ml H2O) was added dropwise over 1 h until excess oxidant was in evidence (starch-iodide paper). The reaction mixture was cooled to room temperature and the resultant violet crystals were collected, washed thoroughly with water and dried (0.52 g, 92%), m.p. 237° C.; δH (200 MHz, d6-DMSO) 1.51-2.19 (7H, m, C6H7), 4.51 (2H, d, OCH2, J=5.66 Hz), 5.82 (2H, br s, C2H2), 7.95 (2H, br s, NH2), 8.15 (1H, br s, NH), 10.21 (1H, br s, NH); m/z (+EI) 249 (M+, 22%), 155 (M+-C7H11, 60), 138 (M+-C7H11O, 100), 69 (24).

Workup

  1. customthe resultant violet crystals were collected
  2. washwashed thoroughly with water
  3. customdried (0.52 g, 92%), m.p. 237° C.

Sources & evidence

ORD record
ord-1ff210f97769496ab2fed79423ed4e23
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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