Diisopropylethylamine → HCID 59627386, compound

HRID 1042272Notes

Reaction equation

HRID 1042272 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:4][N:3]=1.[CH3:18][C:19]1[CH:28]=[CH:27][C:26]2[C:25]([NH:29][C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:31]=3[CH3:40])=[N:24][CH:23]=[CH:22][C:21]=2[C:20]=1[NH2:41].CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:41][C:20]2[C:21]3[CH:22]=[CH:23][N:24]=[C:25]([NH:29][C:30]4[CH:35]=[C:34]([C:36]([F:39])([F:37])[F:38])[CH:33]=[CH:32][C:31]=4[CH3:40])[C:26]=3[CH:27]=[CH:28][C:19]=2[CH3:18])[C:5]([C:9]2[C:10]3[CH:17]=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67368479HCID 67368479, compoundHCID 86649312HCID 86649312, compound2×

Product 1

HCID 59627386HCID 59627386, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(2,4-dichloropyrimidin-5-yl)-7H-pyrrolo[2,3-d]pyrimidine (89 mg, 335 μmol) and 6-methyl-N1-(2-methyl-5-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine (111 mg, 335 μmol) in DMSO (2 mL) was treated with DIPEA (0.3 mL). The mixture was heated to 70° C. in an oil bath for 2 days. Additional quantities of 4-(2,4-dichloropyrimidin-5-yl)-7H-pyrrolo[2,3-d]pyrimidine (3×20 mg) were added during the course of the reaction. The reaction mixture was cooled to rt and poured onto 50 g of ice with 20 mL of NaHCO3. The resulting suspension was extracted with EtOAc (3×50 mL). The EtOAc solution was washed with brine then dried over Na2SO4 and concentrated. The residue was purified via prep LCMS on silica [4% 1M NH3-MeOH in DCM-EtOAc (5-1)]. The residue was further purified by trituation in MeOH to give the title compound as a light yellow solid. MS (ESI, pos. ion) m/z: 561.2 [M+H]+

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe resulting suspension was extracted with EtOAc (3×50 mL)
  3. washThe EtOAc solution was washed with brine
  4. dry with materialthen dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified via prep LCMS on silica [4% 1M NH3-MeOH in DCM-EtOAc (5-1)]
  7. customThe residue was further purified by trituation in MeOH

Sources & evidence

ORD record
ord-ebaa033b802a4106a2a921c8d9ff489e
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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