Diisopropylethylamine → Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate

HRID 1746662Notes

Reaction equation

HRID 1746662 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[C:11]([O:15][C:16](=[O:26])[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:16](=[O:26])[O:15][C:11]([CH3:13])([CH3:14])[CH3:12])=[CH:20][CH:21]=2)=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 59447092Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution of 6-chloropyrimidine-4-carbonyl chloride in DCM (30 mL), obtained as described above for Intermediate 7, step 1 (1.43 g; 8.10 mmol) was added dropwise, during a period of 15 minutes, a solution of (4-amino-benzyl)-carbamic acid tert-butyl ester (Astatech, 1.50 g; 6.75 mmol) and DIEA (2.33 ml; 13.5 mmol) in DCM (5 mL). At the end of addition the reaction mixture was concentrated in vacuo, diluted with water and extracted with EtOAc. The resulting precipitate was filtered and dried under vacuum. The mother liquors were dried on MgSO4, concentrated under vacuum to give a residue, which was precipitated from cyclohexane. The two solids were combined to give the title compound as a brown solid.

Workup

  1. customobtained
  2. additionwas added dropwise, during a period of 15 minutes
  3. additionAt the end of addition the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additiondiluted with water
  6. extractionextracted with EtOAc
  7. filtrationThe resulting precipitate was filtered
  8. customdried under vacuum
  9. customThe mother liquors were dried on MgSO4
  10. concentrationconcentrated under vacuum
  11. customto give a residue, which
  12. customwas precipitated from cyclohexane

Sources & evidence

ORD record
ord-483bb22539914245828e337677a80dc7
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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