Acetic Acid → HCID 22063001, compound

HRID 1827727Notes

Reaction equation

HRID 1827727 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[N:17]=[C:18]([NH2:27])[C:19]2[CH:25]=[C:24](N)[CH:23]=[N:22][C:20]=2[N:21]=1.CC(O)=O.CCN(CC)CC>CN(C=O)C.O>[NH2:15][C:16]1[N:17]=[C:18]([NH2:27])[C:19]2[CH:25]=[C:24]([NH:14][CH:1]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:23]=[N:22][C:20]=2[N:21]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7036BenzhydrylamineHCID 8471TriethylamineHCID 10821153HCID 10821153, compound

Product 1

HCID 22063001HCID 22063001, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of benzhydrylamine (366 mg, 2.0 mmol) and 2,4,6-triaminopyrido[2,3-d]pyrimidine (350 mg, 2.0 mmol) in a mixture of DMF (40 mL) and glacial AcOH (4 mL) is treated with BH3.Et3N (75 mg, 6.6 mmol), and the mixture is stirred at room temperature overnight, then diluted with H2O (20 mL) to decompose any unreacted reducing agent. The solvents are evaporated under reduced pressure, and the residue is purified on a silica gel column using 5-15% CHCl3 in MeOH as the eluent. Pooling and evaporation of appropriate fractions yields the title compound, N-(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)benzhydrylamine.

Workup

  1. additionis treated with BH3
  2. customThe solvents are evaporated under reduced pressure
  3. customthe residue is purified on a silica gel column
  4. customPooling and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-cc4555a984094c1495eec4b1bbdf1468
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

Loading…