Water → HCID 69026224, compound

HRID 219753Notes

Reaction equation

HRID 219753 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]([CH3:21])[CH2:19][OH:20])[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CS([C:35]1[N:40]=[C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:38]=[CH:37][N:36]=1)(=O)=O.[OH2:49]>O1CCCC1>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][C@@H:18]([CH3:21])[CH2:19][O:20][C:35]3[N:40]=[C:39]([O:41][C:42](=[O:49])[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[CH:38]=[CH:37][N:36]=3)[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962Water2×HCID 113575332-Methylsulfonyl-4-benzyloxy-pyrimidineHCID 69025424(R)-3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propan-1-olHCID 178418339Butyllithium

Product 1

HCID 69026224HCID 69026224, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.05 g of (R)-3-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-2-methyl-propan-1-ol (3.02 mmol) were dissolved in 8 ml of tetrahydrofuran. At 0° C., 1.71 ml (3.37 mmol) of n-butyllithium (2 M in pentane) were added within 15 minutes. 0.85 g of 2-methylsulfonyl-4-benzyloxy-pyrimidine (3.21 mmol), dissolved in 5 ml of tetrahydrofurane, were added. Stirring continued for 16 h at room temperature. By cooling with, 2 ml of water were added. The obtained mixture was poured into 15 ml of water and extracted three times with 15 ml of diethyl ether each. The organic layers were combined, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified via silica gel chromatography with dichloromethane, dichloromethane/ethyl acetate 9:1, and dichlormethane/ethyl acetate 3:2 to yield 0.83 g of the product.

Workup

  1. additionwere added
  2. additionwere added
  3. extractionextracted three times with 15 ml of diethyl ether each
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified via silica gel chromatography with dichloromethane, dichloromethane/ethyl acetate 9:1, and dichlormethane/ethyl acetate 3:2

Sources & evidence

ORD record
ord-00ac25f94b0e43e1a6cf2a87cf0a35d2
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

Loading…