Dichloromethane → HCID 25182621, compound

HRID 1746687Notes

Reaction equation

HRID 1746687 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.[CH:10]1([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]([C:23](O)=[O:24])[CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C.C(Cl)Cl>CN(C=O)C>[CH:10]1([NH:16][C:17]2[N:22]=[CH:21][N:20]=[C:19]([C:23]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=3[CH3:9])=[O:24])[CH:18]=2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 178194-Amino-m-cresolHCID 594470756-(Cyclohexylamino)pyrimidine-4-carboxylic acid

Product 1

HCID 25182621HCID 25182621, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-m-cresol (Fluka, 40.00 mg; 0.32 mmol), 6-(cyclohexylamino)pyrimidine-4-carboxylic acid, Intermediate 4 (86.2 mg; 0.39 mmol) and triethylamine (136 μl; 0.97 mmol) in dry DMF (5.00 mL) was treated with polymer-supported Mukaiyama reagent (520 mg; 0.65 mmol) and stirred for 16 hours. DCM was added to the reaction mixture and the solution was filtered through a SPE-NH2 column (2 g). The DCM was evaporated in vacuo, the resulting solution was diluted with EtOAc, washed three times with brine, then the organic phase was dried over magnesium sulfate, filtered and evaporated in vacuo. The solid obtained was triturated in acetonitrile to afford the title compound as a yellow solid.

Workup

  1. filtrationthe solution was filtered through a SPE-NH2 column (2 g)
  2. customThe DCM was evaporated in vacuo
  3. additionthe resulting solution was diluted with EtOAc
  4. washwashed three times with brine
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe solid obtained
  9. customwas triturated in acetonitrile

Sources & evidence

ORD record
ord-e3ce5288c67346bc8cd53fb89821f55f
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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