Dichloromethane → HCID 25183073, compound

HRID 1746663Notes

Reaction equation

HRID 1746663 reaction equation
[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=1.C(N(CC)CC)C.C(Cl)Cl>CN(C=O)C>[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:21][C:22]3[CH:29]=[CH:28][C:25]([CH2:26][OH:27])=[CH:24][CH:23]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 693314-Aminobenzyl alcoholHCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2×

Product 1

HCID 25183073HCID 25183073, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(cyclohexyl-cyclopropylmethyl-amino)-pyrimidine-4-carboxylic acid (Intermediate 13, 1.00 g; 3.63 mmol) in dry DMF (100 ml) was treated with polymer-supported Mukaiyama reagent, prepared as described in “S. Crosignani et al. Org. Lett. 2004, 6(24), 4579-4582” (2987 mg; 6.54 mmol), 4-aminobenzyl alcohol (Fluka, 492 mg; 3.99 mmol) and triethylamine (1.52 ml; 10.9 mmol). The reaction mixture was then stirred at room temperature for 18 hours. DCM was added and the product was filtered through an SPE column (Isolute NH2, 10g) and the column washed with DCM. The mixture was concentrated then rediluted in EtOAc. The organic phase was washed 5 times with brine, dried over MgSO4 and the solvent removed under vacuum to give the title compound (990 mg, 72%).

Workup

  1. customprepared
  2. filtrationthe product was filtered through an SPE column (Isolute NH2, 10g)
  3. washthe column washed with DCM
  4. concentrationThe mixture was concentrated
  5. additionthen rediluted in EtOAc
  6. washThe organic phase was washed 5 times with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-2e263dfb05ba4517bfafc8a39e90f164
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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