Cyclohexanemethanol → HCID 12986177, compound

HRID 1838969Notes

Reaction equation

HRID 1838969 reaction equation
[Na].[NH2:2][C:3]1[N:8]=[C:7](Cl)[C:6]([CH:10]=[O:11])=[C:5]([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1.[CH:27]1([CH2:33][OH:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>>[NH2:2][C:3]1[N:8]=[C:7]([O:34][CH2:33][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:6]([CH:10]=[O:11])=[C:5]([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:4]=1

Participants

4

Reactant 3

HCID 7507CyclohexanemethanolHCID 5360545SodiumHCID 54512249HCID 54512249, compound

Product 1

HCID 12986177HCID 12986177, compound

Procedure

Cyclohexylmethanol (10 ml) and sodium (5 eq; 0.163 g) were reacted at 90° C. for 1 h. 2-Amino-4-chloro-6dibenzylamino-5-pyrimidine carbaldehyde (0.5 g; 1.42 mmol) was added and heating continued for 90 mins. Excess alcohol was removed by short path distillation under reduced pressure, and the product purified further by column chromatography. Product was shown to be contaminated with cyclohexylmethanol by visualisation of the alcohol with sulfuric acid spray (2%).

Workup

  1. temperatureheating
  2. customExcess alcohol was removed by short path distillation under reduced pressure
  3. customthe product purified further by column chromatography

Sources & evidence

ORD record
ord-41f45bcd96374429b99542a3a1289775
Source dataset
uspto-grants-2004_01
Patent number
US06677345B1

Reaction notes

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