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Potassium Carbonate → 3-[5-Cyclopropyl-3-(2,6-difluoro-pyridin-4-ylmethyl)-2,6-dioxo 1,2,3,6tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile

HRID 426255
Notes
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Reaction equation

HRID 426255 reaction equation
[CH:1]1([C:4]2[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=2[C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:17]#[N:18])=[O:13])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1[CH:36]=[C:35]([F:37])[N:34]=[C:33]([F:38])[CH:32]=1.[I-].[Li+]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([C:4]2[C:9](=[O:10])[NH:8][C:7](=[O:11])[N:6]([CH2:30][C:31]3[CH:36]=[C:35]([F:37])[N:34]=[C:33]([F:38])[CH:32]=3)[C:5]=2[C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:17]#[N:18])=[O:13])[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 591846774-(Bromomethyl)-2,6-difluoropyridineHCID 591847043-(5-Cyclopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Product 1

HCID 250296833-[5-Cyclopropyl-3-(2,6-difluoro-pyridin-4-ylmethyl)-2,6-dioxo 1,2,3,6tetrahydro-pyrimidine-4-carbonyl]-5-methyl-benzonitrile
Yield 9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(5-Cyclopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (10 mg, 0.034 mmol) was dissolved in 0.5 mL DMF. Potassium carbonate (4.7 mg, 1 eq.) and 4-bromomethyl-2,6-difluoro-pyridine (7 mg, 1 eq.) were added to the reaction, followed by lithium iodide (4.5 mg, 1 eq.) The reaction was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, followed by washing with brine. The organic layer was concentrated down and purified by reversed phase HPLC (MeCN/water) to give white powder (1.2 mg, 9%). LC-MS shows 420.9 (M−1). 1H NMR (300 MHz, CD3OD): δ 8.40 (s, 1H), 7.97 (s, 1H), 7.79 (s, 1H), 7.76 (s, 1H), 6.58 (s, 2H), 4.85 (s, 2H), 2.44 (s, 3H), 1.01 (m, 1H), 0.72 (m, 3H), 0.43 (m, 1H).

Workup

  1. washby washing with brine
  2. concentrationThe organic layer was concentrated down
  3. custompurified by reversed phase HPLC (MeCN/water)

Sources & evidence

ORD record
ord-e07ea8ff283443009773b7099daacf2c
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106064B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes