2-Chloro-4-(thiophen-2-yl)pyrimidine → [1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-(4-thiophen-2-yl-pyrimidin-2-yl)-amine

HRID 2264400Notes

Reaction equation

HRID 2264400 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]1)[CH3:14]>CC(N(C)C)=O>[CH2:13]([O:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:19][N:20]1[CH2:21][CH2:22][CH:23]([NH:26][C:2]2[N:7]=[C:6]([C:8]3[S:9][CH:10]=[CH:11][CH:12]=3)[CH:5]=[CH:4][N:3]=2)[CH2:24][CH2:25]1)[CH3:14]

Participants

4

Reactant 2

HCID 141179412-Chloro-4-(thiophen-2-yl)pyrimidineHCID 392574451-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine2×

Product 1

HCID 68778571[1-(3-Ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-(4-thiophen-2-yl-pyrimidin-2-yl)-amineYield 18.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-chloro-4-thiophen-2-yl-pyrimidine (29.5 mg, 0.15 mmol, 1.0 equiv) and 1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-ylamine (47.6 mg, 0.18 mmol, 1.2 equiv; intermediate A1) in DMAc (2 mL) was heated by microwave irradiation to 220° C. for 30 min. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 11.5 mg (15%) of the title compound. MS (ISP): 425.3 [M+H]+.

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and purification by preparative HPLC on reversed phase
  3. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-3e550b138d7140e0bbc72ce54e176368
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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