Ethanol → 6-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil

HRID 891233Notes

Reaction equation

HRID 891233 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[O:15])[N:5]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:4](=[O:23])[CH:3]=1.O.C(O)C.[N:28]([O-])=[O:29].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:7]([CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6](=[O:15])[N:5]([CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C:4](=[O:23])[C:3]=1[N:28]=[O:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 222449716-Amino-1,3-bis(cyclohexylmethyl)uracilHCID 23668193Sodium Nitrite

Product 1

HCID 222449706-Amino 1,3-bis(cyclohexylmethyl)-5-nitrosouracil

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-Amino-1,3-bis(cyclohexylmethyl)uracil (from step (b), 25.0 g) was dissolved in glacial acetic acid (440 ml), water (440 ml) and ethanol (440 ml) at reflux. To this solution was added sodium nitrite (5.65 g). The resulting mixture was stirred as it cooled slowly to ambient temperature. The lavender precipitate was filtered off, washed with 1:1 water-ethanol and dried to give 6-amino-1,3-bis(cyclohexylmethyl)-5-nitrosouracil as light purple crystals (23.46 g, 86%), m.p. 240–243° C. dec with effervescence; 1H-NMR (DMSO-d6) δ: 13.23 (br s, 1, ═NOH), 9.00 (br s, 1, ═NH), 3.73 (br t, J=6.86, 4, 2 NCH2), 2.0–1.6 and 1.7–1.1 (both m, total 22, 2 cyclohexyl).

Workup

  1. filtrationThe lavender precipitate was filtered off
  2. washwashed with 1:1 water-ethanol
  3. customdried

Sources & evidence

ORD record
ord-64bfeb30a9cd471e851ad710a257105e
Source dataset
uspto-grants-2006_02
Patent number
US07002012B2

Reaction notes

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