(S)-(+)-Tetrahydrofurfurylamine → HCID 59333732, compound

HRID 1930573Notes

Reaction equation

HRID 1930573 reaction equation
FC(F)(F)S(O[C:7]1[C:8]2[CH2:28][N:27]([C:29](=[O:31])[CH3:30])[CH2:26][CH2:25][C:9]=2[N:10]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][CH:23]=[N:22][CH:21]=3)=[CH:16][CH:15]=2)[N:12]=1)(=O)=O.[O:34]1[CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:39][NH2:40]>CS(C)=O>[O:24]1[C:20]([C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:11]3[N:12]=[C:7]([NH:40][CH2:39][C@@H:35]4[CH2:36][CH2:37][CH2:38][O:34]4)[C:8]4[CH2:28][N:27]([C:29](=[O:31])[CH3:30])[CH2:26][CH2:25][C:9]=4[N:10]=3)=[CH:15][CH:16]=2)=[CH:21][N:22]=[CH:23]1

Participants

4

Reactant 2

HCID 641530(S)-(+)-TetrahydrofurfurylamineHCID 593337606-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 59333732HCID 59333732, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Acetyl-2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate (35 mg, 0.07 mmol, Example 26a) in DMSO (1 mL) was dispensed in a library plate. (S)-(tetrahydrofuran-2-yl)methanamine (7.08 mg, 0.07 mmol) was added to the plate and it was left to shake overnight at 80° C., filtered and purified by preparative HPLC to give (S)-1-(2-(4-(oxazol-5-yl)phenylamino)-4-((tetrahydrofuran-2-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (12.7 mg, 40.4%).

Workup

  1. waitwas left
  2. filtrationfiltered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ff9b474d87594592bddea37874cd891d
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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