Potassium Carbonate → 1-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro-, 6-(5-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-3-(1,1-dimethylethyl)-2-methoxyphenyl)-2-naphthalenyl ester

HRID 341637Notes

Reaction equation

HRID 341637 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N:24]2[CH:29]=[CH:28][C:27](=[O:30])[NH:26][C:25]2=[O:31])[CH:8]=[C:9]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:23])[CH:19]=3)[CH:14]=2)[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:38][C:39]([F:54])([S:50](F)(=[O:52])=[O:51])[C:40]([F:49])([F:48])[C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43]>>[F:54][C:39]([F:38])([S:50]([O:23][C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:9]3[CH:8]=[C:7]([N:24]4[CH:29]=[CH:28][C:27](=[O:30])[NH:26][C:25]4=[O:31])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:10]=3[O:11][CH3:12])[CH:14]=2)[CH:19]=1)(=[O:52])=[O:51])[C:40]([F:48])([F:49])[C:41]([F:47])([F:46])[C:42]([F:45])([F:44])[F:43]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 566406701-(3-tert-butyl-5-(6-hydroxynaphthalen-2-yl)-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 566406691-Butanesulfonic acid, 1,1,2,2,3,3,4,4,4-nonafluoro-, 6-(5-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-3-(1,1-dimethylethyl)-2-methoxyphenyl)-2-naphthalenyl ester

Procedure

A reactor was equipped with an overhead stirrer in the central neck and charged with 45.0 g of 1-(3-tert-butyl-5-(6-hydroxynaphthalen-2-yl)-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (97.8 weight %, 106 mmol, 1.0 equivalent) and 21.9 g of 325 mesh potassium carbonate (159 mmol, 1.5 equivalents). The atmosphere was purged with nitrogen gas while the solids were stirred. The flask was charged with 445 mL of N,N-dimethylformamide, and the slurry was stirred to dissolve the 1-(3-tert-butyl-5-(6-hydroxynaphthalen-2-yl)-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione. The purge was stopped and the reaction was conducted under a slight positive pressure of nitrogen gas. Perfluorobutanesulfonyl fluoride (35.2 g, 117 mmol, 1.1 equivalents) was added in one portion, and the mixture was stirred vigorously to mix the immiscible liquids overnight.

Workup

  1. customA reactor was equipped with an overhead stirrer in the central neck
  2. customThe atmosphere was purged with nitrogen gas while the solids
  3. additionThe flask was charged with 445 mL of N,N-dimethylformamide
  4. stirringthe slurry was stirred
  5. dissolutionto dissolve the 1-(3-tert-butyl-5-(6-hydroxynaphthalen-2-yl)-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione
  6. stirringthe mixture was stirred vigorously
  7. additionto mix the immiscible liquids overnight

Sources & evidence

ORD record
ord-34031b2dbfec4d23b508f388f2a04de6
Source dataset
uspto-grants-2014_11
Patent number
US08895737B2

Reaction notes

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