6-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidine → 3-[3-(2,4-bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl]-6-(2-fluoro-phenyl)-3H-pyrrolo[3,2-d]pyrimidine

HRID 2408480Notes

Reaction equation

HRID 2408480 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:81])([F:80])[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[CH:67]=[C:66]([CH2:68]OS(C2C=CC(C)=CC=2)(=O)=O)[O:65][N:64]=1>>[F:81][C:52]([F:51])([F:80])[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[CH: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)[O:65][N:64]=1

Participants

4

Reactant 3

HCID 674703356-(2-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidineHCID 86688863Toluene-4-sulfonic acid 3-(2,4-bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl esterHCID 178489934HCID 178489934, compound

Product 1

HCID 547599523-[3-(2,4-bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl]-6-(2-fluoro-phenyl)-3H-pyrrolo[3,2-d]pyrimidineYield 7%

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 (100 mg, 0.46 mmol) and toluene-4-sulfonic acid 3-(2,4-bis-trifluoromethylphenyl)-isoxazol-5-ylmethyl ester (322 mg, 0.7 mmol) to produce the desired product (16.1 mg, 7%). 1H-NMR: (d6-DMSO, 400 MHz) δ 9.58 (s, 1H), 9.40 (s, 1H), 8.26 (s, 1H), 8.24 (d, 1H), 8.16 (dt, 1H), 7.83 (d, 1H), 7.72 (m, 1H), 7.58 (s, 1H), 7.52 (d, 1H), 7.44 (d, 1H) 7.13 (d, 1H), 6.20 (s, 2H). LCMS calculated for C24H13F7N4O 506.4, found 507.09 (M+H)+.

Workup

  1. customPrepared analogously to the method

Sources & evidence

ORD record
ord-6b3291e77c7c4ffa8c94b982a21b43f8
Source dataset
uspto-grants-2014_08
Patent number
US08815858B2

Reaction notes

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