(3R)-(+)-3-(Dimethylamino)pyrrolidine → HCID 20594519, compound

HRID 1370068Notes

Reaction equation

HRID 1370068 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]#[N:15])=[CH:12][N:11]=[C:10]([NH:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][N:21]=[CH:20]4)[N:9]=2)=[CH:4][N:3]=1.[CH3:26][N:27]([CH3:33])[C@@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1>>[C:14]([C:13]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:30]3[CH2:31][CH2:32][C@@H:28]([N:27]([CH3:33])[CH3:26])[CH2:29]3)=[N:3][CH:4]=2)=[N:9][C:10]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][N:21]=[CH:20]3)=[N:11][CH:12]=1)#[N:15]

Participants

3

Reactant 2

HCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 18516857HCID 18516857, compound

Product 1

HCID 20594519HCID 20594519, compound

Procedure

4-(2-Chloropyridin-5-yl)-5-cyano-N-(indazol-5-yl)pyrimidine-2-amine (522 mg, 1.5 mmol) and 3-(R)-dimethylaminopyrrolidine were heated together at 140° in a sealed flask for 2 h. On cooling the reaction mixture was triturated with water to give a brown solid which was collected and subjected to column chromatography (silica gel; 1% triethylamine-10% methanol-89% dichloromethane) to give the title compound (417 mg) as a yellow solid m.p.249-250°. δH (d6DMSO) 13.00 (1H, br s), 10.32 (1H, s), 8.81 (2H, d, J 9.2 Hz), 8.15-8.12 (2H, m), 8.04 (1H, s), 7.59 (1H, m), 7.52 (1H, d, J 9.8 Hz), 6.63 (1H, d, J 9.0 Hz), 3.77-3.67 (2H, m), 3.41-3.24 (2H, m), 2.82 (1H, br m), 2.22 (6H, s), 2.21 (1H, m) and 1.84 (1H, m).

Workup

  1. temperatureOn cooling the reaction mixture
  2. customwas triturated with water
  3. customto give a brown solid which
  4. customwas collected

Sources & evidence

ORD record
ord-478b678d691944e2add43807b19952c4
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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