1,1'-Carbonyldiimidazole → 2-(2-Pyrimidyl)aminoethyl alpha-cyclohexylphenylglycolate

HRID 1074156Notes

Reaction equation

HRID 1074156 reaction equation
[CH:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[C:8]([OH:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1N=CN(C(N2C=NC=C2)=O)C=1.O[CH2:31][CH2:32][NH:33][C:34]1[N:39]=[CH:38][CH:37]=[CH:36][N:35]=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[CH:12]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:11])[C:8]([O:10][CH2:31][CH2:32][NH:33][C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[O:9])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 97700(+-)-Cyclohexylphenylglycolic acidHCID 5727142-(Pyrimidin-2-ylamino)ethanol

Product 1

HCID 221558682-(2-Pyrimidyl)aminoethyl alpha-cyclohexylphenylglycolate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of α-cyclohexylphenylglycolic acid (1 g) and N,N-carbonyldiimidazole (0.69 g) in DMF (10 ml), 2-(2-hydroxyethyl) aminopyrimidine (0.6 g) and DBU (0.65 g) were added. The mixture was treated according to the method described in Example 3a, affording 2-(2-pyrimidyl)aminoethyl α-cyclohexylphenylglycolate, which was heated with ethanolic HCl to afford 1,5 g of the hydrochloride. M.p. 167°-168° C.

Workup

  1. additionwere added
  2. additionThe mixture was treated

Sources & evidence

ORD record
ord-c5cb22826df543c895d84be9fa23a3b8
Source dataset
uspto-grants-1990_11
Patent number
US04973592

Reaction notes

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