1,4-Dibromobutane → 2-(Butyloxy)-8-(methyloxy)-9-[4-(1-piperidinyl)butyl]-9H-purin-6-amine formic acid salt

HRID 590436Notes

Reaction equation

HRID 590436 reaction equation
N1([CH2:5][CH2:6][CH2:7][N:8]2[C:16]([O:17][CH3:18])=[N:15][C:14]3[C:9]2=[N:10][C:11]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])=[N:12][C:13]=3[NH2:19])CCC1.FC(F)(F)[C:27]([OH:29])=[O:28].C(O[C:37]1[NH:38][C:39](N)=C2C(N=1)=NC(OC)=N2)CCC.Br[CH2:50][CH2:51][CH2:52][CH2:53]Br.N1CCCCC1>>[CH:27]([OH:29])=[O:28].[CH2:21]([O:20][C:11]1[N:10]=[C:9]2[C:14]([N:15]=[C:16]([O:17][CH3:18])[N:8]2[CH2:7][CH2:6][CH2:5][CH2:37][N:38]2[CH2:39][CH2:53][CH2:52][CH2:51][CH2:50]2)=[C:13]([NH2:19])[N:12]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 80561,4-DibromobutaneHCID 8082PiperidineHCID 592526009-[3-(1-Azetidinyl)propyl]-2-(butyloxy)-8-(methyloxy)-9H-purin-6-amineHCID 178450357HCID 178450357, compound

Product 1

HCID 667270062-(Butyloxy)-8-(methyloxy)-9-[4-(1-piperidinyl)butyl]-9H-purin-6-amine formic acid salt

Procedure

Prepared similarly to Intermediate 20 from 2-(butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate, 1,4-dibromobutane and piperidine but with sequential mass directed autopreparations using Method A followed by Method D.

Sources & evidence

ORD record
ord-cb6cbd25cc7149b28ef1d58ff26a502e
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

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