Sodium Hydroxide → HCID 178507957, compound

HRID 1711967Notes

Reaction equation

HRID 1711967 reaction equation
O.[NH2:2][C:3]1[CH:8]=[C:7]([OH:9])[N:6]=[C:5]([SH:10])[N:4]=1.[OH-].[Na+].[F:13][C:14]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br>O.O1CCCC1>[NH2:2][C:3]1[N:4]=[C:5]([S:10][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:14]=2[F:13])[N:6]=[C:7]([OH:9])[CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 5179841-(Bromomethyl)-2,3-difluoro-benzeneHCID 178507962HCID 178507962, compound

Product 1

HCID 178507957HCID 178507957, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred suspension of 4-amino-6-hydroxy-2-mercaptopyrimidine monohydrate (67.7 g) in a mixture of water (920 ml) and tetrahydrofuran (300 ml) was added aqueous sodium hydroxide solution (46-48% w/w; 24 ml) followed by water (40 ml). The resulting hazy, pale yellow solution was cooled to 20° C. before adding 2,3-difluorobenzyl bromide (83.0 g) uniformly over 25 minutes, to yield a white precipitate. The mixture was stirred at ambient temperature for 3.5 hours, the product collected and washed twice with a mixture of water (68 ml) and tetrahydrofuran (24 ml), to afford the title compound as a white solid (101.89 g).

Workup

  1. customto yield a white precipitate
  2. customthe product collected
  3. washwashed twice with a mixture of water (68 ml) and tetrahydrofuran (24 ml)

Sources & evidence

ORD record
ord-0b0395d2f6da49a798e2a19abbcdaecb
Source dataset
uspto-grants-2010_09
Patent number
US07790883B2

Reaction notes

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