Pivaloyl chloride → HCID 21112409, compound

HRID 1767130Notes

Reaction equation

HRID 1767130 reaction equation
[CH2:1]([C:8]1[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]([O:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:10]([OH:26])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(C)(C)C.Cl[CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>C1COCC1>[CH2:1]([C:8]1[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[C:11]([O:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])=[C:10]([O:26][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 767274-(2-Chloroethyl)morpholine2×HCID 178499083HCID 178499083, compound

Product 1

HCID 21112409HCID 21112409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-benzyl-5-[(tert-butoxycarbonyl)oxy]-6-hydroxypyrimidine-4-carboxylate (N-1) (prepared from B-5 in Example 3, Step 1 by protection of the 5-hydroxyl group with pivaloyl chloride using a procedure similar to those set forth in Example 6, Step 2) in THF, CsCO3 (2 eq.) and 4-(2-chloroethyl)morpholine (1.5 eq.) hydrochloride were added and mixture reacted at 60° C. for 1 h. Further addition of 4-(2-chloroethyl)morpholine (1 eq.) allowed the complete consumption of starting material after 2 h. The mixture was then allowed to cool to room temperature, poured into EtOAc, extracted with brine, dried (Na2SO4), filtered and concentrated.

Workup

  1. custommixture reacted at 60° C. for 1 h
  2. customthe complete consumption of starting material after 2 h
  3. additionpoured into EtOAc
  4. extractionextracted with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cd7429a64fd34b6d988542ddd6eae975
Source dataset
uspto-grants-2007_06
Patent number
US07232819B2

Reaction notes

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