Water → tert-Butyl [2,6-dimethyl-4-(5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-phenoxy]acetate

HRID 81502Notes

Reaction equation

HRID 81502 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH3:16][C:17]1[CH:22]=[C:21]([C:23]2[O:24][C:25]3[N:26]=[C:27]([S:36][CH3:37])[N:28]=[C:29]([O:32][CH2:33][CH2:34][CH3:35])[C:30]=3[N:31]=2)[CH:20]=[C:19]([CH3:38])[C:18]=1[OH:39].O>CN(C)C=O>[CH3:16][C:17]1[CH:22]=[C:21]([C:23]2[O:24][C:25]3[N:26]=[C:27]([S:36][CH3:37])[N:28]=[C:29]([O:32][CH2:33][CH2:34][CH3:35])[C:30]=3[N:31]=2)[CH:20]=[C:19]([CH3:38])[C:18]=1[O:39][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 136389866HCID 136389866, compound

Product 1

HCID 86688232tert-Butyl [2,6-dimethyl-4-(5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.20 g of potassium carbonate and then 0.93 ml of tert-butyl bromoacetate were added to a solution of 2.00 g of 2,6-dimethyl-4-(5-methylsulfanyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)phenol in 20 ml of N,N-dimethylformamide. The mixture was reacted at 60° C. for 1 h and then allowed to cool and poured into water. The precipitate obtained was filtered off with suction and dried under reduced pressure. This gave 2.45 g of the title compound.

Workup

  1. customThe mixture was reacted at 60° C. for 1 h
  2. temperatureto cool
  3. customThe precipitate obtained
  4. filtrationwas filtered off with suction
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-1fe2590e9b5b43a697d634712d8aefba
Source dataset
uspto-grants-2014_09
Patent number
US08846691B2

Reaction notes

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