Dimethylamine → HCID 58786845, compound

HRID 2114789Notes

Reaction equation

HRID 2114789 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[N:11]=[C:12]([C@@H:19]3[CH2:23][C@@H:22]([O:24][CH3:25])[CH2:21][NH:20]3)[N:13]([CH3:18])[C:14](=[O:17])[C:15]=2[OH:16])=[O:9])=[CH:4][CH:3]=1.[CH2:28]([N:30](CC)[CH2:31]C)C.Cl[C:36](=[O:41])[C:37](OC)=[O:38].CNC.C1COCC1>>[CH3:28][N:30]([C:36](=[O:41])[C:37]([N:20]1[CH2:21][C@H:22]([O:24][CH3:25])[CH2:23][C@H:19]1[C:12]1[N:13]([CH3:18])[C:14](=[O:17])[C:15]([OH:16])=[C:10]([C:8]([NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:27][CH:26]=2)=[O:9])[N:11]=1)=[O:38])[CH3:31]

Participants

6

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 54677480HCID 54677480, compound

Product 1

HCID 58786845HCID 58786845, compound

Conditions

Temperature
0 °C

Procedure

To N-(4-fluorobenzyl)-5-hydroxy-2-[(2S,4R)-4-methoxypyrrolidin-2-yl]-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide, triethylamine (1 eq.) was added. The reaction mixture was cooled down to 0° C. and methyl chlorooxoacetate (3 eq.) was added. After 1 hour the reaction mixture was concentrated and a big excess of dimethylamine 2M in THF (30 eq.) was added The reaction mixture was concentrated and the desired compound was isolated by HPLC purification (Waters, Symmetry C18, 5 um, 19×50 mm eluting with water and acetonitrile containing 0.1% trifluoroacetic acid) as a 2:8 mixture of rotamers by NMR:

Workup

  1. concentrationAfter 1 hour the reaction mixture was concentrated
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-102a3d2ab9774b148351cc5a40f35512
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

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