Sodium Hydroxide → [1,3]Dioxolan-2-ylmethyl-(5,6-diphenyl-furo[2,3-d]pyrimidin-4-yl)-amine

HRID 502669Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.Br[CH2:24][CH:25]1[O:29][CH2:28][CH2:27][O:26]1.[OH-].[Na+]>CN(C=O)C>[O:26]1[CH2:27][CH2:28][O:29][CH:25]1[CH2:24][NH:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:9]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred mixture of 4-amino-5,6-diphenylfuro[2,3-d]pyrimidine (100 mg, 0.34 mmol), 2-bromomethyl-1,3-dioxolane (116 mg, 0.69 mmol) and sodium hydroxide granules (42 mg, 1.05 mmol) in DMF (1.5 mL) was heated at 150° C. for 1 hour. The resulting mixture was filtered and purified by preparative HPLC to give a beige solid (73 mg). 1H NMR (CDCl3): 8.50 (1H, s), 7.62-7.49 (7H, m), 7.32-7.25 (3H, m), 5.70 (1H, br s), 5.00 (1H, br s), 3.85-3.63 (6H, m). LC/MS: 374 (MH+).

Workup

filtrationThe resulting mixture was filtered
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-3d087fa02640403bbae0549581e65ec2
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776867B2

Reaction notes

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