tert-Butanol → HCID 59405031, compound

HRID 1892184Notes

Reaction equation

HRID 1892184 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-460c3a62410b44bdbb0f3d8d31c5b14c
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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