Potassium Carbonate → HCID 86633451, compound

HRID 1668658Notes

Reaction equation

HRID 1668658 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N:3]=1.[NH:16]1[C:24]2[C:19](=[C:20]([CH2:25][NH2:26])[CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17]1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N:3]=[C:2]([NH:26][CH2:25][C:20]2[CH:21]=[CH:22][CH:23]=[C:24]3[C:19]=2[CH:18]=[CH:17][NH:16]3)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 280302(1H-indol-4-yl)methanamineHCID 15766443HCID 15766443, compound2×

Product 1

HCID 86633451HCID 86633451, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4,6-dichloro-2-(6-methyl-pyridin-2-yl)-pyrimidine (Intermediate E) (1 eq, 0.417 mmol, 0.1 g) and C-(1H-indol-4-yl)-methylamine (1 eq, 0.417 mmol, 61 mg) and K2CO3 (1 eq, 0.417 mmol, 58 mg) in NMP (1 ml) is heated using microwave radiation at 120° C. for 1 hour. After cooling to room temperature, the mixture is partitioned between DCM/water and the organic portion is separated and concentrated in vacuo. The crude brown oil is purified by flash chromatography on silica eluting with 100% DCM and the appropriate fractions are combined and concentrated in vacuo. The resulting oil is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are concentrated in vacuo and the residue is dissolved in DCM and concentrated in vacuo once again. The resulting solid is dried under vacuum to afford the title compound [M+H]+=350/352.

Workup

  1. customat 120° C.
  2. customfor 1 hour
  3. customthe mixture is partitioned between DCM/water
  4. customthe organic portion is separated
  5. concentrationconcentrated in vacuo
  6. customThe crude brown oil is purified by flash chromatography on silica eluting with 100% DCM
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting oil is dissolved in MeOH
  9. washeluting with MeOH
  10. concentrationThe methanolic ammonia fractions are concentrated in vacuo
  11. dissolutionthe residue is dissolved in DCM
  12. concentrationconcentrated in vacuo once again
  13. customThe resulting solid is dried under vacuum

Sources & evidence

ORD record
ord-7b65008e805b4274a0da6b0baccf7f87
Source dataset
uspto-grants-2011_08
Patent number
US07989458B2

Reaction notes

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