Potassium Carbonate → HCID 178433128, compound

HRID 1371114Notes

Reaction equation

HRID 1371114 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[NH4+:18].[OH-].C([O-])([O-])=O.[K+].[K+]>>[CH3:8][C:6]1[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]2=[C:2]([NH2:18])[N:7]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 178432852HCID 178432852, compound

Product 1

HCID 178433128HCID 178433128, compoundYield 5.4%

Procedure

This compound was prepared according to the method described in Example 26 by employing 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (0.10 g, 0.41 mmol) with NH4OH (Aldrich Chemical Company) (2.5 mL, 21.4 mmol) and K2CO3 (0.33 g, 2.4 mmol). The crude reaction mixture was concentrated to dryness and the residue extracted with hot MeOH and concentrated. The resulting yellow oil was purified by flash chromatography on silica gel (1:40 MeOH/CH2Cl2 followed by 1:20 MeOH/CH2Cl2) to give 0.005 g (5%) of the title compound as an off-white solid. Mp: >280° C. 1H NMR (CD3OD; 500 MHz): δ 2.53 (s, 3), 6.74 (s, 1), 7.44 (t, 1, J=7.2), 7.52 (t, 2, J=7.5), 7.82 (d, 2, J=7.5); MS m/z: 225 (M+1).

Workup

  1. customThis compound was prepared
  2. customThe crude reaction mixture
  3. concentrationwas concentrated to dryness
  4. extractionthe residue extracted with hot MeOH
  5. concentrationconcentrated
  6. customThe resulting yellow oil was purified by flash chromatography on silica gel (1:40 MeOH/CH2Cl2 followed by 1:20 MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cf799b3325ab4d01b2a78ffa83778238
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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