4-Aminobenzyl alcohol → (4-(4-Chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)methanol

HRID 2093028Notes

Reaction equation

HRID 2093028 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C@H](NC(=O)OC(C)(C)C)C)=[CH:15][CH:14]=2)[N:3]=1.NC1C=CC([CH2:34][OH:35])=CC=1>>[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:34][OH:35])=[CH:15][CH:14]=2)[N:3]=1

Participants

3

Reactant 2

HCID 693314-Aminobenzyl alcoholHCID 57584789(R)-tert-butyl 1-(4-(4-chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)ethylcarbamate

Product 1

HCID 57584696(4-(4-Chloro-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)methanol

Procedure

C7 was prepared in a manner similar to that described in for making C3 in Step 3 of Example 1 except that 4-aminobenzyl alcohol (2.4 g, 19 mmol) was used instead of C2. When the reaction was complete the reaction mixture was concentrated and dissolved in EtOA. The resultant solution was washed with water, brine, dried over MgSO4, and concentrated. The resultant tan solid was triterated with ether and a small amount of EtOAc, filtered and concentrated to provide C7 as a tan solid. Yield: 2.98 g, 50%. MS+ 304.1. 1H NMR (500 MHz, d6-DMSO) δ: 10.61 (s, 1H), 8.76 (s, 1H), 7.59 (d, 2H), 7.26 (d, 2H), 5.10 (bs, 1H), 4.43 (s, 2H).

Workup

  1. customC7 was prepared in a manner similar to
  2. concentrationwas concentrated
  3. dissolutiondissolved in EtOA
  4. washThe resultant solution was washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. filtrationa small amount of EtOAc, filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a0676e94cf6b436bbf540978fe0ff0e5
Source dataset
uspto-grants-2013_05
Patent number
US08440822B2

Reaction notes

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