Potassium Carbonate → 3-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzoic acid

HRID 1049889Notes

Reaction equation

HRID 1049889 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH2:12])[C:10]=2[N:11]=1.B([C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([F:25])[CH:24]=1)[C:19]([OH:21])=[O:20])(O)O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[NH2:12][C:9]1[C:10]2[N:11]=[C:2]([C:16]3[CH:17]=[C:18]([CH:22]=[C:23]([F:25])[CH:24]=3)[C:19]([OH:21])=[O:20])[CH:3]=[CH:4][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 447172053-Borono-5-fluorobenzoic acidHCID 867038966-Chloropyrido[3,2-d]pyrimidin-4-amine

Product 1

HCID 727035203-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

6-chloropyrido[3,2-d]pyrimidin-4-amine (500 mg, 2.8 mmol) 3-A in acetonitrile (5 mL) was treated with 3-borono-5-fluoro-benzoic acid (CAS 269404-73-6) (560 mg, 3 mL), PDCL2(DPPF) (202 mg, 0.28 mmol) and 1 M potassium carbonate solution (8 mL). The reaction vial was purged with nitrogen, and heated to 80° C. for 1 hour. LCMS showed 100% conversion to desired product. Yellow precipitate was collected and LCMS indicated it is pure product 3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-5-fluorobenzoic acid 3. The filtrate was concentrate and purified by prep HPLC. LC/MS (ESI+): m/z 285 (M+H).

Workup

  1. customThe reaction
  2. customvial was purged with nitrogen
  3. customYellow precipitate was collected
  4. concentrationThe filtrate was concentrate
  5. custompurified by prep HPLC

Sources & evidence

ORD record
ord-38253dae6e8b45daa03518a32ac42b5e
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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