tert-Butanol → HCID 59405031, compound

HRID 2387986Notes

Reaction equation

HRID 2387986 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][C:7](=[O:24])[NH:8][C:9]3[CH:16]=[C:15]([Cl:17])[C:14]([CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])=[CH:13][C:10]=3[C:11]=2[N:12]=1.Br[C:26]1[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=1.C(O)(C)(C)C.CC(C)([O-])C.[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.O>[Cl:17][C:15]1[C:14]([CH2:18][CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])=[CH:13][C:10]2[C:11]3[N:12]=[C:2]([NH:1][C:26]4[C:27]([CH3:32])=[N:28][CH:29]=[CH:30][CH:31]=4)[N:3]=[CH:4][C:5]=3[CH2:6][C:7](=[O:24])[NH:8][C:9]=2[CH:16]=1

Participants

8

Reactant 4

HCID 6386tert-Butanol2×HCID 12010033-Bromo-2-methylpyridineHCID 23665647Potassium tert-butoxideHCID 59405010HCID 59405010, compound

Product 1

HCID 59405031HCID 59405031, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 2-amino-9-chloro-10-[3-(dimethylamino)propyl]-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (0.10 g, 0.29 mmol), Xphos (8.6 mg, 0.018 mmol), tris(dibenzylideneacetone)dipalladium (4.7 mg, 0.0052 mmol) and 3-bromo-2-methylpyridine (50 mg, 0.29 mmol) in a dry, sealed microwave tube under an atmosphere of argon was added tert-butyl alcohol (1.0 mL) followed by a 1.0 M solution of potassium tert-butoxide in tert-butyl alcohol (0.58 mL, 0.58 mmol). The mixture was heated under microwave irradiation at 150° C. for 30 min. The reaction mixture was allowed to cool to rt and then added to water (50 mL). The precipitated solid was collected via suction filtration, washed with water, and dried to produce 9-chloro-10-[3-(dimethylamino)propyl]-2-[(2-methylpyridin-3-yl)amino]-5,7-dihydro-6H-pyrimido[5,4-d][1]benzazepin-6-one (95 mg, 0.21 mmol, 75%) as a brown solid. LCMS (FA): m/z=453.5 (M+H).

Workup

  1. customsealed microwave tube under an atmosphere of argon
  2. temperatureto cool to rt
  3. filtrationThe precipitated solid was collected via suction filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-e2589c10c94a4203a9a4caa18f9e6c7f
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

Loading…