1,2-Dimethoxyethane → 5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4 (3H)-one
Reaction equation
Br[C:2]1[O:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:10])[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1(C)C(C)(C)OB([C:26]2[CH:39]=[CH:38][C:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=2)O1.C(=O)([O-])[O-].[K+].[K+].COCCOC>O>[C:12]1([C:3]2[C:4]3[C:9](=[O:10])[NH:8][CH:7]=[N:6][C:5]=3[O:11][C:2]=2[C:26]2[CH:27]=[CH:28][C:29]([O:30][CH2:31][CH2:32][N:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)=[CH:38][CH:39]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Into a 16×100 mm vial sparged with argon was placed 6-bromo-5-phenylfuro[2,3-d]pyrimidin-4 (3H)-one 45 (250 mg, 0.859 mmol), 1-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)pyrrolidine (409 mg, 1.29 mmol), palladiumtetrakistriphenylphosphine (100 mg, 0.086 mmol), potassium carbonate (1.18 g, 8.59 mmol), DME (4 mL), and water (1 mL). The vial was capped and heated to 75° C. for 20 hours.
Workup
- customInto a 16×100 mm vial sparged with argon
- customThe vial was capped
Sources & evidence
- ORD record
- ord-2fdc932bf8d04879818e926511d92b90
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776867B2
Reaction notes
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