(S)-2-Methylpyrrolidine 4-methylbenzenesulfonate → 2-chloro-7-(4-fluorophenyl)-4-((S)-2-methylpyrrolidin-1-yl)-5,7-dihydrofuro[3,4-d]pyrimidine

HRID 475784Notes

Reaction equation

HRID 475784 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][O:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:30][C@H:31]1[CH2:35][CH2:34][CH2:33][NH:32]1>>[Cl:1][C:2]1[N:3]=[C:4]([N:32]2[CH2:33][CH2:34][CH2:35][C@@H:31]2[CH3:30])[C:5]2[CH2:10][O:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 44118660(S)-2-Methylpyrrolidine 4-methylbenzenesulfonateHCID 580754962,4-Dichloro-7-(4-fluorophenyl)-5,7-dihydrofuro[3,4-d]pyrimidine

Product 1

HCID 580757242-chloro-7-(4-fluorophenyl)-4-((S)-2-methylpyrrolidin-1-yl)-5,7-dihydrofuro[3,4-d]pyrimidine

Procedure

2,4-dichloro-7-(4-fluorophenyl)-5,7-dihydrofuro[3,4-d]pyrimidine (Preparation M) was reacted as described in Preparation Hp1 and Hp2 with (S)-2-methylpyrrolidine p-toluenesulfonate salt to afford 2-chloro-7-(4-fluorophenyl)-4-((S)-2-methylpyrrolidin-1-yl)-5,7-dihydrofuro[3,4-d]pyrimidine (Preparation Me) as a mixture of 2 diasteriomers. LC-MS (M+H)+=334.1.

Sources & evidence

ORD record
ord-08ed773abf474f4da3a16a7557db56e4
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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