Benzene, 1-bromo-3,5-dimethyl- → 2-Chloro-5-methyl-N-(3,5-dimethylphenyl)pyrimidin-4-amine

HRID 1097100

Reaction equation

HRID 1097100 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[Cl:10][C:11]1[N:16]=[C:15]([NH2:17])[C:14]([CH3:18])=[CH:13][N:12]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[K+]>O1CCOCC1.CC(O)=O.CC(O)=O.[Pd]>[Cl:10][C:11]1[N:16]=[C:15]([NH:17][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=2)[C:14]([CH3:18])=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 43021752-Chloro-5-methylpyrimidin-4-amineHCID 23665647Potassium tert-butoxide

Product 1

HCID 575164912-Chloro-5-methyl-N-(3,5-dimethylphenyl)pyrimidin-4-amineYield 50%

Reagents, catalysts & solvents 2

HCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-bromo-3,5-dimethylbenzene (104 μL, 0.77 mmol), 2-chloro-5-methyl-pyrimidin-4-ylamine (104 mg, 0.72 mmol), Pd(OAC)2 (15 mg, 0.07 mmol), Xantphos (83 mg, 0.14 mmol) and potassium tert-butoxide (159 mg, 1.42 mmol) in dioxane (8 mL) was microwaved at 160° C. for 20 min. The reaction mixture was cooled to room temperature and filtered rinsing with DCM and methanol. The filtrate was concentrated and purified using gradient flash chromatography (0-100% ethyl acetate in hexanes) to afford the title compound as a yellow oil (89 mg, 50%). MS (ES+): m/z 248 (M+H)+.

Workup

  1. customwas microwaved at 160° C. for 20 min
  2. filtrationfiltered
  3. washrinsing with DCM and methanol
  4. concentrationThe filtrate was concentrated
  5. custompurified

Sources & evidence

ORD record
ord-6fefd455f0944d6d8ed4417907290bf8
Source dataset
uspto-grants-2012_03
Patent number
US08138199B2

Linked notes

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