Ammonium Chloride → HCID 86621762, compound

HRID 1092225Notes

Reaction equation

HRID 1092225 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[N:15]=[C:14]([NH:16][C@H:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH3:18])[N:13]=[C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:11]=3[N+:31]([O-])=O)[CH:5]=2)[CH2:3][CH2:2]1.[NH4+].[Cl-]>CCO.C1COCC1.[Zn]>[NH2:31][C:11]1[C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:13][C:14]([NH:16][C@H:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH3:18])=[N:15][C:10]=1[NH:9][C:6]1[CH:5]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[NH:8][N:7]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86621768HCID 86621768, compound

Product 1

HCID 86621762HCID 86621762, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (S)-ethyl 6-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-[1-(4-fluorophenyl)ethylamino]-5-nitropyrimidine-4-carboxylate (Method 10; 0.7 g, 1.5 mmol) and zinc dust (0.5 g, 7.7 mmol) in EtOH:THF (1:1, 20 ml) was slowly added saturated aqueous NH4Cl solution (3 ml). After 1 hour, the reaction mixture was cooled to 0° C., to which was added saturated NH4OAc solution (10 ml). The resulting mixture was allowed to stir for 10 minutes at 0° C. and 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 the title compound (0.60 g, 92%) which was used without further purification.

Workup

  1. filtrationfiltered 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

Sources & evidence

ORD record
ord-c3fc6c2f91d749198de999662ff6e175
Source dataset
uspto-grants-2012_03
Patent number
US08129403B2

Reaction notes

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