3-(2,4-Bis-trifluoromethyl-phenyl)-6-chloromethyl-pyridazine → 3-[6-(2,4-Bis-trifluoromethylphenyl)-pyridazin-3-ylmethyl]-6-(2-fluorophenyl)-3H-pyrrolo[3,2-d]pyrimidine

HRID 2408481Notes

Reaction equation

HRID 2408481 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:72])([F:71])[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[N:64]=[N:65][C:66]([CH2:69]Cl)=[CH:67][CH:68]=1>>[F:72][C:52]([F:51])([F:71])[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[N:64]=[N:65][C:66]([CH2:69][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)=[CH:67][CH:68]=1

Participants

4

Reactant 3

HCID 249967593-(2,4-Bis-trifluoromethyl-phenyl)-6-chloromethyl-pyridazineHCID 674703356-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidineHCID 178489934HCID 178489934, compound

Product 1

HCID 547597703-[6-(2,4-Bis-trifluoromethylphenyl)-pyridazin-3-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 3-(2,4-Bis-trifluoromethylphenyl)-6-chloromethylpyridazine (383 mg, 1.12 mmol) to obtained desired product (9 mg, 5%).

Workup

  1. customPrepared analogously to the method

Sources & evidence

ORD record
ord-ed50149085874e609388b3531bbc28ed
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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