Sodium Bicarbonate → HCID 86715513, compound

HRID 2284600Notes

Reaction equation

HRID 2284600 reaction equation
ClC1C2N=C(Cl)C=CC=2N=CN=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]=[CH:19][N:20]=[C:21]([O:24][CH3:25])[C:22]=2[N:23]=1.C([O-])(O)=O.[Na+]>CO>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[N:18]=[CH:19][N:20]=[C:21]([O:24][CH3:25])[C:22]=2[N:23]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86715514HCID 86715514, compound

Product 1

HCID 86715513HCID 86715513, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-4-methoxypyrido[3,2-d]pyrimidine 4,6-Dichloropyrido[3,2-d]pyrimidine (prepared from Int'l Pat. App. Pubs. nos. 2005058913, 2011131741 and 201009469) (2.5 g, 12.4 mmol) and NaHCO3 (3.1 g, 31 mmol) in MeOH (20 mL) were heated at 70° C. for 12 h under nitrogen atmosphere. The reaction mixture was filtered and concentrated the filtrate. The crude concentrate was diluted with water and filtered. The suction dried solid was stirred in EtOAc (20 mL) and filtered to obtain 6-chloro-4-methoxypyrido[3,2-d]pyrimidine (1.8 g) as an off-white solid. 1H NMR (300 MHz, DMSO-d6): δ 8.88 (s, 1H), 8.37 (d, J=8.8 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H), 4.14 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated the filtrate
  3. concentrationThe crude concentrate
  4. additionwas diluted with water
  5. filtrationfiltered
  6. customThe suction dried solid
  7. filtrationfiltered

Sources & evidence

ORD record
ord-81171845cac4438389511a14506a9d37
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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