Sodium Carbonate → 5H-Pyrrolo3,2-dpyrimidine, 7-bromo-2-fluoro-4-(phenylmethoxy)-5-(phenylmethoxy)methyl-

HRID 1349350Notes

Reaction equation

N[C:2]1[N:3]=[C:4]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:5]2[N:10]([CH2:11][O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[C:8]([Br:20])[C:6]=2[N:7]=1.N1C=CC=CC=1.[FH:35].N(OC(C)(C)C)=O.C([O-])(O)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>N1C=CC=CC=1>[CH2:22]([O:21][C:4]1[C:5]2[N:10]([CH2:11][O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:9]=[C:8]([Br:20])[C:6]=2[N:7]=[C:2]([F:35])[N:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of the product from Example 11.2 (0.9 g) in dry pyridine (40 mL) was cooled in an ice bath while hydrogen fluoride-pyridine (˜65%) (15 mL) was added slowly keeping the temperature ≦10° C. The resulting solution was cooled to 0° C., tert-butyl nitrite (3 mL) was added, and the solution was stirred in the ice bath for 3 h and then poured carefully onto saturated aq NaHCO3 (500 mL) adding Na2CO3 as required to keep the solution basic. The mixture was extracted (×2) with chloroform which was dried and concentrated to dryness. Chromatography gave 4-benzyloxy-5-N-benzyloxymethyl-7-bromo-2-fluoropyrrolo[3,2-d]pyrimidine (0.63 g) as a solid. 13C NMR (CDCl3) δ 158.5 (JC,F=17 Hz), 157.5 (JC,F=213 Hz), 150.6 (JC,F=16 Hz), 136.8, 135.5, 133.9, 129.1, 128.9, 128.9, 128.5, 127.9, 114.1, 91.9, 77.9, 71.1, 70.0.

Workup

additionwas added slowly
customthe temperature ≦10° C
extractionThe mixture was extracted (×2) with chloroform which
customwas dried
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-10243aa08dd14766aef6f9bbfb8b7bd4
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211677B2

Reaction notes

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