4-Amino-1-Boc-piperidine → 4-[4-Amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1371667Notes

Reaction equation

HRID 1371667 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4](S(CC)=O)[N:3]=1.NC1C(C(C2C=C(F)C=CC=2OC)=O)=CN=C(S(CC)(=O)=O)N=1.[NH2:46][CH:47]1[CH2:52][CH2:51][N:50]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:49][CH2:48]1>CN1CCCC1=O.O>[C:56]([O:55][C:53]([N:50]1[CH2:51][CH2:52][CH:47]([NH:46][C:4]2[N:3]=[C:2]([NH2:1])[C:7]([C:8](=[O:9])[C:10]3[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=3[O:17][CH3:18])=[CH:6][N:5]=2)[CH2:48][CH2:49]1)=[O:54])([CH3:59])([CH3:57])[CH3:58]

Participants

6

Reactant 3

HCID 12682914-Amino-1-Boc-piperidineHCID 10314106(4-Amino-2-ethanesulfinyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanoneHCID 10472348(4-Amino-2-ethanesulfonyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanone

Product 1

HCID 119749544-[4-Amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

A solution composed of a 9:1 mixture of (4-amino-2-ethanesulfinyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanone and (4-amino-2-ethanesulfonyl-pyrimidin-5-yl)-(5-fluoro-2-methoxy-phenyl)-methanone (11.6 g, 36 mmol, Example 163) and 4-amino-1-N-Boc-piperidine (Astatech Inc.) (10.8 g, 54 mmol) in 1-methyl-2-pyrrolidinone (50 mL, Aldrich) was heated at 70° C. for 30 minutes. The reaction was diluted with water and extracted with ethyl acetate. The dried (Na2SO4) organic solution was evaporated and the residue was triturated with ethyl ether/hexane to give 95% yield of 4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless solid, mp 122–124 dec. Mass Spectrum (LR-ES) M+: 445.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe dried (Na2SO4) organic solution
  3. customwas evaporated
  4. customthe residue was triturated with ethyl ether/hexane

Sources & evidence

ORD record
ord-2d9707b7a99a4605a2d3f1d90ce4fcb3
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

Loading…