Triethylamine → Methyl 2-[[1-[4-[[[(4-fluorophenyl)methyl]amino]carbonyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-2-pyrimidinyl]-1-methylethyl]amino]-2-oxoacetate

HRID 1351378Notes

Reaction equation

HRID 1351378 reaction equation
[NH2:1][C:2]([C:5]1[N:6]([CH3:24])[C:7](=[O:23])[C:8]([OH:22])=[C:9]([C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[O:12])[N:10]=1)([CH3:4])[CH3:3].C(N(CC)CC)C.Cl[C:33](=[O:38])[C:34]([O:36][CH3:37])=[O:35]>C(Cl)(Cl)Cl>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][NH:13][C:11]([C:9]2[N:10]=[C:5]([C:2]([NH:1][C:33](=[O:38])[C:34]([O:36][CH3:37])=[O:35])([CH3:4])[CH3:3])[N:6]([CH3:24])[C:7](=[O:23])[C:8]=2[OH:22])=[O:12])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 547218802-(2-Aminopropan-2-yl)-N-[(4-fluorophenyl)methyl]-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Product 1

HCID 54737243Methyl 2-[[1-[4-[[[(4-fluorophenyl)methyl]amino]carbonyl]-1,6-dihydro-5-hydroxy-1-methyl-6-oxo-2-pyrimidinyl]-1-methylethyl]amino]-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 2-(1-amino-1-methylethyl)-N-(4-fluorobenzyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine4-carboxamide (4) and triethyl amine (3 eq) in chloroform, methyl chlorooxoacetate (1.5 eq) was added with an external cooling. Finished the addition, the ice bath was removed and the mixture was stirred at room temperature for 3 h. Reaction mixture was then partitioned between chloroform and 1N HCl. Organic layer was separated, washed with brine, dried (Na2SO4), filtered and concentrated to obtain title product.

Workup

  1. additionwas added with an external cooling
  2. additionthe addition
  3. customthe ice bath was removed
  4. customReaction mixture
  5. customwas then partitioned between chloroform and 1N HCl
  6. customOrganic layer was separated
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c917ba314ebe4fcda22c6c7413a2d9d2
Source dataset
uspto-grants-2007_05
Patent number
US07217713B2

Reaction notes

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