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

HRID 1835003Notes

Reaction equation

HRID 1835003 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) a 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-226f35e493d8458c8b0116a4c5a8c080
Source dataset
uspto-grants-2004_08
Patent number
US06770267B2

Reaction notes

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