Benzylamine → HCID 71736172, compound

HRID 338780Notes

Reaction equation

HRID 338780 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([OH:17])=O)[CH2:9][CH2:8][C:6]=2[N:7]=1.C(N(CC)CC)C.CCCP(=O)=O.[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:11][N:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([NH:41][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:17])[CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 866958153-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzoic acid

Product 1

HCID 71736172HCID 71736172, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-(2-amino-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzoic acid (54 mg, 0.20 mmol), triethylamine (0.084 mL, 0.60 mmol), and catalytic DMAP in 4.5 mL CH2Cl2 at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.131 mL, 0.22 mmol). After 5 min at rt, benzyl amine (0.023 mL, 0.21 mmol) was added and the reaction stirred at rt for 23 hours. The reaction was partitioned between EtOAc and aqueous Na2CO3 solution, the EtOAc layer washed with aqueous NaHCO3 solution, H2O, brine, dried with anhydrous Na2SO4 and evaporated to a solid. The solid was chromatographed eluting with CHCl3/EtOAc plus 5% MeOH and then triturated with acetone/hexane to give the title compound as a light beige solid (20 mg, 28%). 1H NMR (Acetone-d6) δ: 8.39 (br. s., 1H), 8.12 (s, 1H), 7.58 (br. s., 1H), 7.27-7.38 (m, 5H), 7.16-7.26 (m, 2H), 4.59 (d, J=5.6 Hz, 2H), 4.30 (s, 2H), 3.66 (t, J=5.3 Hz, 2H), 2.82 (t, J=5.3 Hz, 2H).

Workup

  1. customThe reaction was partitioned between EtOAc and aqueous Na2CO3 solution
  2. washthe EtOAc layer washed with aqueous NaHCO3 solution, H2O, brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customevaporated to a solid
  5. customThe solid was chromatographed
  6. washeluting with CHCl3/EtOAc plus 5% MeOH
  7. customtriturated with acetone/hexane

Sources & evidence

ORD record
ord-6c1e39c22c284b43b2fbbfd2be16d37f
Source dataset
uspto-grants-2014_11
Patent number
US08889870B2

Reaction notes

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