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

HRID 502670Notes

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][C:25]1([CH3:30])[O:29][CH2:28][CH2:27][O:26]1.[OH-].[Na+]>CN(C=O)C>[C:11]1([C:10]2[C:3]3[C:2]([NH:1][CH2:24][C:25]4([CH3:30])[O:29][CH2:28][CH2:27][O:26]4)=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred mixture of 4-amino-5,6-diphenylfuro[2,3-d]pyrimidine (50 mg, 0.17 mmol), 2-bromomethyl-2-methyl-[1,3]dioxolane (prepared according to Visweswariah et al., Synthesis, 1982, 4, 309-310) (38 mg, 0.21 mmol) and sodium hydroxide granules (21 mg, 0.53 mmol) in DMF (1 mL) was heated in a microwave at 120° C. for 5 minutes. The resulting mixture was filtered and purified by preparative HPLC to give a beige solid (9 mg). 1H NMR (CDCl3): 8.39 (1H, s), 7.52-7.41 (7H, m), 7.23-7.18 (3H, m), 5.05 (1H, br s), 3.77-3.63 (4H, m), 3.50 (2H, m), 1.19 (3H, s). LC/MS: 388 (MH+).

Workup

filtrationThe resulting mixture was filtered
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-c9d719d5a9d94fada853f6a7f3de5a82
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776867B2

Reaction notes

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