Water → 5-(2(S)-amino-3-phenylprop-1-yl)amino-8-(2-naphthyl)-7-(4-pyridyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897415Notes

Reaction equation

HRID 897415 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:12]2[N:13]([CH:25]=[N:26][N:27]=2)[C:14](SC)=[N:15][C:16]=1[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[C:28]1([CH2:34][C@H:35]([NH2:38])[CH2:36][NH2:37])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C=O)C>[NH2:38][C@@H:35]([CH2:34][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:36][NH:37][C:14]1[N:13]2[CH:25]=[N:26][N:27]=[C:12]2[C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[C:16]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12699301(2S)-3-Phenylpropane-1,2-diamineHCID 22346600HCID 22346600, compound

Product 1

HCID 101740625-(2(S)-amino-3-phenylprop-1-yl)amino-8-(2-naphthyl)-7-(4-pyridyl)-1,2,4-triazolo[4,3-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-(2-naphthyl)-5-methylthio-7-(4-pyridyl)-1,2,4-triazolo[4,3-c]pyrimidine (350 mg, 1 mmol), K3CO3 (100 mg) and (2S)-3-phenylpropane-1,2-diamine (150 mg, 1 mmol) were combined in dry DMF (ca. 5 mL) and the mixture was stirred at room temperature for 48 h. To the reaction solution was added water (ca. 10 mL) at RT and a precipitate formed. The suspension was stirred at RT for 1 h. The solid was filtered off and washed with water (3×10 ml) and dried under vacuum at 50° C. overnight; MS (m/z) 472.3 (M+H)+; C29H25N7 requir. 471.56.

Workup

  1. customa precipitate formed
  2. stirringThe suspension was stirred at RT for 1 h
  3. filtrationThe solid was filtered off
  4. washwashed with water (3×10 ml)
  5. customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record
ord-38571b4443c047e98c4b3e33a91d5f2d
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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