Ammonium Chloride → (R)-2-[5-amino-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-6-methylpyrimidin-2-ylamino]-2-(4-fluorophenyl)ethanol

HRID 1092224Notes

Reaction equation

HRID 1092224 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([N+:16]([O-])=O)=[C:14]([CH3:19])[N:13]=[C:12]([NH:20][C@H:21]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[CH2:22][OH:23])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-]>[Zn].CO.C1COCC1>[NH2:16][C:15]1[C:10]([NH:9][C:6]2[CH:5]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[NH:8][N:7]=2)=[N:11][C:12]([NH:20][C@H:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:22][OH:23])=[N:13][C:14]=1[CH3:19]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 66589226HCID 66589226, compound

Product 1

HCID 66589221(R)-2-[5-amino-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-6-methylpyrimidin-2-ylamino]-2-(4-fluorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a suspension of (R)-2-[4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-6-methyl-5-nitropyrimidin-2-ylamino]-2-(4-fluorophenyl)ethanol (Method 1, 1.0 g, 2.4 mmol) and zinc dust (0.79 g, 12.0 mmol) in the mixture of MeOH:THF (1:1, 70 ml) was slowly added saturated NH4Cl solution (10 ml). After 3 hours, the reaction was treated with saturated aqueous NH4OAc solution (40 ml), and the resulting mixture was stirred for 30 minutes. The reaction was then filtered through a plug of celite with EtOAc (100 ml). The resulting aqueous layer was extracted with EtOAc (2×100 ml), dried, filtered, and concentrated to give (0.8 g, 90%). MS: Calcd.: 383; Found: [M+H]+ 384.

Workup

  1. filtrationThe reaction was then filtered through a plug of celite with EtOAc (100 ml)
  2. extractionThe resulting aqueous layer was extracted with EtOAc (2×100 ml)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give (0.8 g, 90%)

Sources & evidence

ORD record
ord-f2b598c7d43548b2b9e563097a5a5601
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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