Ethyl Acetate → N4-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)pyrimidine-4,5-diamine

HRID 1848015Notes

Reaction equation

HRID 1848015 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C:10]2[CH:29]=[CH:28][C:13]3[N:14]=[C:15]([N:17]4[C@@H:21]5[CH2:22][CH2:23][CH2:24][CH2:25][C@H:20]5[O:19][C:18]4([CH3:27])[CH3:26])[S:16][C:12]=3[CH:11]=2)[C:3]=1[N+:30]([O-])=O.CCOC(C)=O>CO.[Pd]>[CH3:26][C:18]1([CH3:27])[N:17]([C:15]2[S:16][C:12]3[CH:11]=[C:10]([CH2:9][NH:8][C:4]4[C:3]([NH2:30])=[CH:2][N:7]=[CH:6][N:5]=4)[CH:29]=[CH:28][C:13]=3[N:14]=2)[C@@H:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C@H:20]2[O:19]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 866810366-chloro-N-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)-5-nitropyrimidin-4-amine

Product 1

HCID 86681037N4-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)pyrimidine-4,5-diamineYield 125.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred mixture of 6-chloro-N-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)-5-nitropyrimidin-4-amine (153 mg, 0.3 mmol) from Step 5 of this Example in MeOH (5 mL) and EtOAc (5 mL) was added Pd 10% wt. on carbon (20 mg, 0.02 mmol). Hydrogen gas was bubbled through the stirred mixture for 2 min, then stirring was continued for 15 h under 1 atm of H2. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford N4-((2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methyl)pyrimidine-4,5-diamine as an oil (155 mg). The material was used in the next step without further purification. LCMS (ESI) m/z 411 (M+H)+.

Workup

  1. customHydrogen gas was bubbled through the stirred mixture for 2 min
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7e7724bbc1f444d091d155d0d3c236e4
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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