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Tetrahydrofuran → 2-[3-(1,3-Thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]propan-2-ol

HRID 1039900
Notes
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Reaction equation

HRID 1039900 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:13]=[C:14]([NH:16][C:17]3[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=3)[CH:15]=2)C(OC)=O)=[CH:4][N:3]=[CH:2]1.[CH2:27]1COCC1.C[Mg]Cl.C([O:38][CH2:39][CH3:40])(=O)C>>[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([C:39]([OH:38])([CH3:40])[CH3:27])[CH:13]=[C:14]([NH:16][C:17]3[N:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=3)[CH:15]=2)=[CH:4][N:3]=[CH:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 67262142Methyl 3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoateHCID 178418332HCID 178418332, compound2×

Product 1

HCID 584564182-[3-(1,3-Thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]propan-2-olYield 74%

Conditions

Temperature
0 °C

Procedure

To a flask containing the product of Step 3 (254 mg, 0.67 mmol) was added THF (6.7 mL). The solution was cooled to 0° C. and then methylmagnesium chloride (3.0M in Et2O, 1.1 mL, 3.3 mmol) was added and the reaction was stirred for one hour. After one hour, more methylmagnesium chloride (3.0M in Et2O, 1.1 mL, 3.3 mmol) was added and the reaction was stirred for 30 minutes. The reaction was then diluted with ethyl acetate and carefully quenched with water and then diluted with water. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated. Flash chromatography was used for purification to yield 2-[3-(1,3-thiazol-5-yl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]propan-2-ol (188 mg, 0.49 mmol, 74% yield). MS ESI: [M+H]+ m/z 381. 1H NMR (500 MHz, DMSO-d6) δ 10.26 (s, 1H), 9.07 (s, 1H), 8.82 (d, J=4.8, 1H), 8.20 (s, 1H), 8.03 (s, 1H), 7.79 (s, 1H), 7.45 (s, 1H), 7.28 (d, J=4.9, 1H), 5.12 (s, 1H), 1.46 (s, 6H).

Workup

  1. waitAfter one hour
  2. stirringthe reaction was stirred for 30 minutes
  3. customcarefully quenched with water
  4. additiondiluted with water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customFlash chromatography was used for purification

Sources & evidence

ORD record
ord-eb3294efdf084a3e93f5763c28dc958a
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes