Water → 5-[4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyridin-2-amine

HRID 2353626Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[N:3]=1.O.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[CH:31][C:32]([NH2:35])=[N:33][CH:34]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.COCCOC.C(O)C>[CH3:14][C@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]1[CH:5]=[C:4]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[N:3]=[C:2]([C:29]2[CH:30]=[CH:31][C:32]([NH2:35])=[N:33][CH:34]=2)[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2-Chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidine (363 mg, 1.19 mmol) was dissolved in a solution of 18% DMF in a mixture of 7:3:2 DME:water:ethanol (7 mL). 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (496 mg, 2.25 mmol), 2M sodium carbonate solution (2 mL) and dichlorobis(triphenylphosphine) palladium (42 mg) were added to the solution and it was heated under reflux at 90° C. for 90 minutes under nitrogen atmosphere. The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL), the organics dried over magnesium sulphate, filtered and concentrated in vacuo to give the desired product as a yellow oil (410 mg) which was used without further purification.

Workup

temperaturewas heated
customThe reaction was partitioned between ethyl acetate (50 mL) and water (50 mL)
dry with materialthe organics dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5faafd70c1a74ce9a77a6b547e1dd6e2
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07750003B2

Reaction notes

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