Pyrrolidine → HCID 18967285, compound

HRID 399564Notes

Reaction equation

HRID 399564 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[N:19]=[C:18]([N:20]4[CH2:25][CH2:24][CH:23](O)[CH2:22][CH2:21]4)[N:17]=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[NH:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1.C([BH3-])#N.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[N:19]=[C:18]([N:20]4[CH2:25][CH2:24][CH:23]([N:49]5[CH2:53][CH2:52][CH2:51][CH2:50]5)[CH2:22][CH2:21]4)[N:17]=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 4

HCID 31268PyrrolidineHCID 159087TriacetoxyperiodinaneHCID 5003444Sodium cyanoborohydrideHCID 18946167HCID 18946167, compound

Product 1

HCID 18967285HCID 18967285, compound

Procedure

Prepared from 4-[(3-chloro-4-fluorophenyl)amino]-6-[4-hydroxy-1-piperidinyl]pyrimido[5,4-d]pyrimidine by oxidation with Dess-Martin reagent and subsequent reductive amination with pyrrolidine and sodium cyanoborohydride. Melting point: 202°-204° C.; Rf : 0.58 (alumina; petroleum ether/ethyl acetate/methanol=10:10:1)

Sources & evidence

ORD record
ord-b6494dd20c954a819fb6821118ca64e4
Source dataset
uspto-grants-1998_10
Patent number
US05821240

Reaction notes

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