Sodium Hydroxide → HCID 178428544, compound
Reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[NH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1.C([O-])(=O)C.[Na+].[OH-].[Na+].C(=O)(O)[O-].[Na+]>O.CC(O)=O>[NH2:1][C:2]1[N:7]=[C:6]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]2)[CH:5]=[C:4]([CH3:9])[N:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 99 °C
Procedure
A suspension mixture of 2-amino-4-chloro-6-methylpyrimidine (144 g, 1.0 mol), trans-4-aminocyclohexanol (140 g, 1.2 mol), AcOH (5 mL) in water (0.6 L) was heated at 99° C. in a 3.0 L flask. After 6 h at same temperature, Sodium acetate (82.0 g, 1 mol) was added to the reaction mixture. After 48 h, at the same temperature aq NaOH (50 mL, 10 N) was added. The reaction mixture was heated to 99° C. for 2 additional days. The reaction can be stopped if 2-amino-4-chloro-6-methylpyrimidine is less than 2% by HPLC analysis. If the reaction is slow another portion of aq. NaOH can be added to the reaction mixture as long as the pH is ˜7 to 8. The reaction mixture was then neutralized with Sodium bicarbonate and cooled to 0° C. Filtration gave trans-4-(2-amino-6-methylpyrimidin-4-ylamino)cyclohexanol (˜85%). Wet material is used for next step.
Workup
- temperatureThe reaction mixture was heated to 99° C. for 2 additional days
- customThe reaction
- additioncan be added to the reaction mixture as long as the pH is ˜7 to 8
- temperaturecooled to 0° C
- filtrationFiltration
Sources & evidence
- ORD record
- ord-770fa53803704dcda5fba16f195e2fb1
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273755B2
Reaction notes
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