Sodium Carbonate → 5-[4-(2-Oxo-2-pyrrolidin-1-ylethoxy)phenyl]pyrimidin-2-amine

HRID 500182

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=2)O1.Br[C:24]1[CH:38]=[CH:37][C:27]([O:28][CH2:29][C:30]([N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:31])=[CH:26][CH:25]=1>O.C(O)C.C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:31]=[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)[CH2:29][O:28][C:27]1[CH:37]=[CH:38][C:24]([C:15]2[CH:20]=[N:19][C:18]([NH2:21])=[N:17][CH:16]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Sodium carbonate (0.318 g, 3.0 mmol) in water (2.0 mL) was added to a mixture of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.221 g, 1.0 mmol), 1-[(4-bromophenoxy)acetyl]pyrrolidine (0.341 g, 1.2 mmol) and tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol) in ethanol (1.5 mL) and toluene (1.5 mL). The resulting mixture was heated at 120° C. for 3 h. The mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue (0.29 g) was directly used in next step without further purification. LCMS: (M+H)=299.1.

Workup

washwashed with water and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue (0.29 g) was directly used in next step without further purification

Sources & evidence

ORD record: ord-fedfaf05f7a944be9a1a0206acd125ee
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Linked notes

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