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

HRID 1049900Notes

Reaction equation

HRID 1049900 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]=[CH:23][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]=[CH:23][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 27339573-Carboxyphenylboronic acidHCID 867038966-Chloropyrido[3,2-d]pyrimidin-4-amine

Product 1

HCID 867039033-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

6-chloropyrido[3,2-d]pyrimidin-4-amine 3-A (500 mg, 2.8 mmol) in acetonitrile (5 mL) was treated with 3-borono-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 ppt. was filtered and LCMS indicated it is pure product 3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)benzoic acid 14. The filtrate was concentrate and purified with reverse phase C-18 column to provide more product. LC/MS (ESI+): m/z 267 (M+H).

Workup

  1. customThe reaction
  2. customvial was purged with nitrogen
  3. filtrationwas filtered
  4. concentrationThe filtrate was concentrate
  5. custompurified with reverse phase C-18 column
  6. customto provide more product

Sources & evidence

ORD record
ord-9d755f0f67e04d329a3f5a7e43c5ed6b
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

Loading…