2-Chloro-4-(thiophen-2-yl)pyrimidine → HCID 68781078, compound

HRID 2264411Notes

Reaction equation

HRID 2264411 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.[Cl:13][C:14]1[CH:27]=[CH:26][C:17]([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]2)=[CH:16][C:15]=1[O:28][CH2:29][CH3:30]>CC(N(C)C)=O>[Cl:13][C:14]1[CH:27]=[CH:26][C:17]([CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([NH:25][C:2]3[N:7]=[C:6]([C:8]4[S:9][CH:10]=[CH:11][CH:12]=4)[CH:5]=[CH:4][N:3]=3)[CH2:21][CH2:20]2)=[CH:16][C:15]=1[O:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 141179412-Chloro-4-(thiophen-2-yl)pyrimidineHCID 592103771-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamine2×

Product 1

HCID 68781078HCID 68781078, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 2-chloro-4-thiophen-2-yl-pyrimidine (49.2 mg, 0.25 mmol, 1.0 equiv; example 4/step 1) and 1-(4-chloro-3-ethoxy-benzyl)-piperidin-4-ylamine (80.6 mg, 0.30 mmol, 1.2 equiv; intermediate A2) in DMAc (2 mL) was heated by microwave irradiation to 220° C. for 1 h. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 14.3 mg (13%) of the title compound. MS (ISP): 429.5 [M+H]+.

Workup

  1. customwas heated by microwave irradiation to 220° C. for 1 h
  2. customRemoval of the solvent
  3. customunder reduced pressure and purification by preparative HPLC on reversed phase
  4. washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record
ord-c1ff5a7907a14fec888ba78190d86e70
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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