Methyl 2,4-dichloropyrimidine-6-carboxylate → methyl 2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylate

HRID 2353636Notes

Reaction equation

HRID 2353636 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:13][C@H:14]1[CH2:19][O:18][CH2:17][CH2:16][NH:15]1>C(Cl)Cl.C(N(CC)CC)C>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][C@@H:14]2[CH3:13])[N:3]=1

Participants

5

Reactant 2

HCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 59379939methyl 2-chloro-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine-4-carboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Methyl 2,6-dichloropyrimidine-4-carboxylate (5.00 g) was dissolved in DCM (120 mL). (3S)-3-Methylmorpholine (2.49 g) dissolved in triethylamine (3.70 mL) and DCM (10 mL) was added dropwise to the solution over 10 minutes. The reaction was left to stir at room temperature for 1 hour then the mixture concentrated in vacuo and dissolved in DCM (300 mL). The organics were washed with water (150 mL) and dried (MgSO4). The crude material was chromatographed on silica, eluting with 2.5% methanol in DCM, to give the desired compound (3.15 g) as a white solid.

Workup

  1. waitThe reaction was left
  2. concentrationthe mixture concentrated in vacuo
  3. dissolutiondissolved in DCM (300 mL)
  4. washThe organics were washed with water (150 mL)
  5. dry with materialdried (MgSO4)
  6. customThe crude material was chromatographed on silica
  7. washeluting with 2.5% methanol in DCM

Sources & evidence

ORD record
ord-952bcc14d9a44bd6b9c899bda223d360
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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