6-Chloro-2-methylpyrimidine-4,5-diamine → HCID 178432856, compound

HRID 1621355Notes

Reaction equation

HRID 1621355 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].[CH:11]([O-])([O-])OCC>>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]2[C:3]=1[N:10]=[CH:11][NH:9]2

Participants

3

Reactant 2

HCID 5941456-Chloro-2-methylpyrimidine-4,5-diamineHCID 53630039Ethylorthoformate

Product 1

HCID 178432856HCID 178432856, compound

Conditions

Temperature
100 °C

Procedure

6-Chloro-2-methylpyrimidine-4,5-diamine (8.89 g, 56.1 mmol, the material from Step 1) was suspended in ethyl orthoformate (100 mL, 601 mmol) in a flask fitted with a reflux condenser and placed in a preheated oil bath (100° C.) and stirred for 75 minutes. Then, the reaction was cooled to room temperature, concentrated, treated with hexanes and filtered. The solid washed with hexanes, collected, and taken on to Step 3. MS (ESI pos. ion) m/z: 169. Calculated exact mass for C6H5ClN4: 168.

Workup

  1. customfitted with a reflux condenser
  2. customplaced in a preheated oil bath
  3. temperatureThen, the reaction was cooled to room temperature
  4. concentrationconcentrated
  5. additiontreated with hexanes
  6. filtrationfiltered
  7. washThe solid washed with hexanes
  8. customcollected

Sources & evidence

ORD record
ord-65d5d594484a48008811718a63242535
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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