Methanol → [5-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanol

HRID 410623Notes

Reaction equation

HRID 410623 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([CH:24]=[O:25])=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.CO.[BH4-].[Na+]>C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[S:23][C:22]([CH2:24][OH:25])=[N:21][CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866582525-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazole-2-carbaldehyde

Product 1

HCID 58456320[5-(3-Methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanolYield 86.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazole-2-carbaldehyde (Example 88, Step 1, 0.15 g, 0.41 mmol) was added methanol (4 mL) and sodium borohydride (0.016 g, 0.41 mmol). Once complete, the reaction was diluted with ethyl acetate, washed carefully with aqueous saturated ammonium chloride, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography to yield [5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanol (0.13 g, 85%). MS ESI: [M+H]+ m/z 366.7. 1H NMR (500 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.83 (d, J=4.8, 1H), 7.98 (s, 2H), 7.45 (s, 1H), 7.28 (d, J=4.9, 1H), 7.17 (s, 1H), 6.10 (t, J=5.8, 1H), 4.71 (d, J=5.8, 2H), 2.31 (s, 3H). rhSYK activity=+++

Workup

  1. washwashed carefully with aqueous saturated ammonium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-80cb2709d1d5487ebb6b24bb8a1bf823
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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