Ammonia → 6-Bromo-pyrido[2,3-d]pyrimidin-4-ylamine

HRID 2284629Notes

Reaction equation

HRID 2284629 reaction equation
[Br:1][C:2]1[CH:12]=[N:11][C:5]2[N:6]=[CH:7][N:8]=[C:9](Cl)[C:4]=2[CH:3]=1.[NH3:13]>CC(O)C>[Br:1][C:2]1[CH:12]=[N:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH2:13])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 529838176-Bromo-4-chloropyrido[2,3-d]pyrimidine

Product 1

HCID 867155386-Bromo-pyrido[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6-Bromo-4-chloropyrido[2,3-d]pyrimidine (1.0 g) and 4% NH3 in i-PrOH (25 mL) were stirred in a sealed tube at room temperature overnight. The pale brown heterogeneous slurry was concentrated, diluted with water and filtered. The brown solid thus collected was suction dried to obtain 6-bromopyrido[2,3-d]pyrimidin-4-amine (1.3 g, purity: 97%). 1H NMR (300 MHz, DMSO-d6) δ 9.09 (d, J=2.5 Hz, 1H), 9.01 (d, J=2.5 Hz, 1H), 8.52 (s, 1H), 8.31 (br s, 2H).

Workup

  1. concentrationThe pale brown heterogeneous slurry was concentrated
  2. additiondiluted with water
  3. filtrationfiltered
  4. customThe brown solid thus collected
  5. customdried

Sources & evidence

ORD record
ord-0308c7787c684ed0912bb0b4200d150f
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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