1,2-Dimethoxyethane → N-isopropyl-5-phenyl-6-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)furo[2,3-d]pyrimidin-4-amine

HRID 502638Notes

Reaction equation

Br[C:2]1[O:14][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]([CH3:13])[CH3:12])[C:4]=2[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC1(C)C(C)(C)OB([C:29]2[CH:42]=[CH:41][C:32]([O:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:31][CH:30]=2)O1.C(=O)([O-])[O-].[K+].[K+].COCCOC>O>[CH:11]([NH:10][C:9]1[C:4]2[C:3]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:2]([C:29]3[CH:30]=[CH:31][C:32]([O:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][CH2:39][CH2:40]4)=[CH:41][CH:42]=3)[O:14][C:5]=2[N:6]=[CH:7][N:8]=1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 75 °C

Procedure

Into a 16×100 mm vial sparged with argon was placed 6-bromo-N-isopropyl-5-phenylfuro[2,3-d]pyrimidin-4-amine (100 mg, 0.301 mmol), 1-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)pyrrolidine (120 mg, 0.361 mmol), palladium tetrakistriphenylphosphine (17 mg, 0.015 mmol), potassium carbonate (125 mg, 0.903 mmol), DME (4 mL), and water (1 mL). The vial was sealed and heated to 75° C. for 24 hours.

Workup

customInto a 16×100 mm vial sparged with argon
customThe vial was sealed

Sources & evidence

ORD record: ord-50b0a70f52624f8d829dbec6fa167111
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776867B2

Reaction notes

Loading…