Methanol → HCID 68325542, compound

HRID 2403322Notes

Reaction equation

HRID 2403322 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C@H:22]3[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]3)=[CH:18][CH:17]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.CO>C1COCC1>[OH:8][C:9]1[CH:14]=[N:13][C:12]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([C@H:22]3[O:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]3)=[CH:20][CH:21]=2)=[N:11][CH:10]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86671409HCID 86671409, compound

Product 1

HCID 68325542HCID 68325542, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-tert-Butyl 2-(4-(5-(benzyloxy)pyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (0.36 g) was combined with MeOH (15 ml) and THF (5 ml) to give a light brown solution. The mixture was degassed by bubbling through argon for several minutes. Palladium on charcoal (41.4 mg, 10%) was added. The reaction mixture was then stirred under a balloon filled with argon overnight. The reaction mixture was then filtered through celite and concentrated in vacuo to afford (R)-tert-butyl 2-(4-(5-hydroxypyrimidin-2-ylamino)phenyl)morpholine-4-carboxylate (311 mg, quant.) as a light brown foam which was used in the next step without further purification. MS (ISP): 373.2 ([M+H]+).

Workup

  1. customto give a light brown solution
  2. customThe mixture was degassed
  3. customby bubbling through argon for several minutes
  4. additionPalladium on charcoal (41.4 mg, 10%) was added
  5. additionfilled with argon overnight
  6. filtrationThe reaction mixture was then filtered through celite and
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9426b30c364042dc9e0e81dfcf860e56
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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