Bromine → HCID 21196285, compound

HRID 1108246Notes

Reaction equation

HRID 1108246 reaction equation
[CH3:1][S:2][C:3]1[N:4]([CH2:13][CH2:14][CH3:15])[C:5](=[O:12])[C:6]2[S:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[Br:16]Br>C(O)(=O)C>[Br:16][C:9]1[C:7]2[N:8]=[C:3]([S:2][CH3:1])[N:4]([CH2:13][CH2:14][CH3:15])[C:5](=[O:12])[C:6]=2[S:11][CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 211838812-(Methylthio)-3-propylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 21196285HCID 21196285, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution containing 1.01 g of the title compound of Step B dissolved in approximately 50 mL of acetic acid cooled to 0° C. was added 0.24 mL of bromine. The mixture was allowed to warm to room temperature and stirred for 24 h. The reaction mixture was filtered to obtain 0.60 g of a white solid. The white solid was purified by column chromatography on silica gel eluting with hexane and then 8:1 hexane:ethyl acetate. Collection and evaporation of those fractions containing the least polar component (according to thin layer chromatography, 6:1 hexane:ethyl acetate mixture as the development solvent) yielded 0.12 g of the title compound of Step C, a compound of the invention, as a white solid melting at 146-147° C. 1H NMR (400 MHz, CDCI3): δ 1.02 (t,3H), 1.81 (m,2H), 2.71 (s,3H), 4.11 (t,2H), 7.69 (s,1H).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-c274d697860b4bdd88ce5d6053596d81
Source dataset
uspto-grants-2000_05
Patent number
US06066638

Reaction notes

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