7-bromo-6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine → 7-Bromo-6-(2-fluorophenyl)-3-[5-(4-methoxy-2-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-ylmethyl]-3H-pyrrolo[3,2-d]pyrimidine

HRID 2408484Notes

Reaction equation

[Br:1][C:2]1[C:6]2[N:7]=[CH:8][N:9]=[CH:10][C:5]=2[NH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:30][C:29]([CH2:31]OS(C)(=O)=O)=[N:28][N:27]=2)=[C:22]([C:37]([F:40])([F:39])[F:38])[CH:21]=1>CN(C=O)C>[Br:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:4][C:5]2[C:6]=1[N:7]=[CH:8][N:9]([CH2:31][C:29]1[S:30][C:26]([C:23]3[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][C:22]=3[C:37]([F:40])([F:38])[F:39])=[N:27][N:28]=1)[CH:10]=2

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of 7-bromo-6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine (152 mg, 0.52 mmol) and methanesulfonic acid 5-(4-methoxy-2-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-ylmethyl ester (211 mg, 0.57 mmol) were stirred in 2 mL DMF at 65° C. for 14 h. The solution was then heated to 85° C. for 4 h and cooled to rt. The resulting solution was filtered and purified by HPLC (10-70% MeCN/H2O with 1% formic acid). Lyophilization of the pure fractions gave 103 mg (0.183 mmol, 35% yield) of the titled compound. 1H NMR (DMSO-d6): 9.15 (s, 1H), 8.96 (s, 1H), 7.72 (d, 1H), 7.64 (t, 1H), 7.55 (q, 1H), 7.43 (s, 1H), 7.32-7.42 (m, 3H), 6.23 (s, 2H), 3.92 (s, 3H). LC-MS calculated for C23H14BrF4N5OS 563.00, found 564.35 [M+H]+.

Workup

temperaturecooled to rt
filtrationThe resulting solution was filtered
custompurified by HPLC (10-70% MeCN/H2O with 1% formic acid)

Sources & evidence

ORD record: ord-1d72337373024a2794b3584c0e3e020b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815858B2

Reaction notes

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