Water → HCID 68325483, compound

HRID 2403324Notes

Reaction equation

HRID 2403324 reaction equation
[F:1][CH:2]([F:30])[O:3][C:4]1[CH:5]=[N:6][C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C@H:17]3[O:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[CH:13][CH:12]=2)=[N:8][CH:9]=1.C(#N)C.O.FC(F)(F)C(O)=O>CCOC(C)=O.C1COCC1>[F:30][CH:2]([F:1])[O:3][C:4]1[CH:5]=[N:6][C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C@H:17]3[O:22][CH2:21][CH2:20][NH:19][CH2:18]3)=[CH:13][CH:12]=2)=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 68325557HCID 68325557, compound

Product 1

HCID 68325483HCID 68325483, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
80 °C

Procedure

(R)-tert-Butyl 2-(4-(5-(difluoromethoxy)pyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (58 mg) was combined with acetonitrile (2 ml) and water (6 ml). Trifluoroacetic acid (138 μl) was added. The vial was capped and shaken at 80° C. for 4 hours. The reaction mixture was then poured into EtOAc/THF (1:1) and washed with 1 M aq. NaOH. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH) to afford (R)-5-(difluoromethoxy)-N-(4-(morpholin-2-yl)phenyl)pyrimidin-2-amine (31 mg, 70%) as a white solid. MS (ISP): 323.1 ([M+H]+).

Workup

  1. customThe vial was capped
  2. washwashed with 1 M aq. NaOH
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash column chromatography (Isolute® Flash-NH2 from Separtis; gradient: heptane/EtOAc/MeOH)

Sources & evidence

ORD record
ord-aaeb6efb572944398889be9327598901
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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