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

HRID 2408479Notes

Reaction equation

HRID 2408479 reaction equation
COC1C=CC(C(C2SC=NN=2)[N:10]2[C:18]3[C:13](=[N:14][CH2:15][NH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])=C(C(F)(F)F)C=1.FC1C=CC=CC=1C1NC2C=NC=NC=2C=1.[F:51][C:52]([F:75])([F:74])[C:53]1[CH:58]=[C:57]([C:59]([F:62])([F:61])[F:60])[CH:56]=[CH:55][C:54]=1[C:63]1[S:67][C:66]([CH2:68]OS(C)(=O)=O)=[N:65][N:64]=1>>[F:75][C:52]([F:51])([F:74])[C:53]1[CH:58]=[C:57]([C:59]([F:62])([F:60])[F:61])[CH:56]=[CH:55][C:54]=1[C:63]1[S:67][C:66]([CH2:68][N:16]2[CH:17]=[C:18]3[N:10]=[C:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[CH:12]=[C:13]3[N:14]=[CH:15]2)=[N:65][N:64]=1

Participants

4

Reactant 3

HCID 674703356-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidineHCID 86688862Methanesulfonic acid [5-(2,4-bis-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-yl]-methanyl esterHCID 178489934HCID 178489934, compound

Product 1

HCID 545760563-[5-(2,4-Bis-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-ylmethyl]-6-(2-fluorophenyl)-3H-pyrrolo[3,2-d]pyrimidineYield 5%

Procedure

Prepared analogously to the method described for 3-[5[(4-methoxy-2-trifluoromethyl-phenyl)-[1,3,4]thiadiazol-2-ylmethyl]-6-(2-fluorophenyl)-3H-pyrrolo[3,2-d]pyrimidine beginning with 6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine (200 mg, 0.93 mmol) and methanesulfonic acid [5-(2,4-bis-trifluoromethylphenyl)-[1,3,4]thiadiazol-2-yl]-methanyl ester (568 mg, 1.40 mmol) which produced 9 mg (5%) of the title compound. LCMS calculated for C23H12F7N5S: 523.4, found 524.01 (M+H)+.

Workup

  1. customPrepared analogously to the method

Sources & evidence

ORD record
ord-00e1394fb77f441ba44ec9b7238e4588
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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