Hydrochloric Acid → 1-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

HRID 1892618Notes

Reaction equation

HRID 1892618 reaction equation
C(OC(N1CCC2C(=CC(OC)=C(OC)C=2)C1CC1C=CC(Br)=CC=1)=O)(C)(C)C.COC1N=C(OC)C(B(O)O)=CN=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+].[C:68]([O:72][C:73]([N:75]1[CH2:84][CH2:83][C:82]2[C:77](=[CH:78][C:79]([O:87][CH3:88])=[C:80]([O:85][CH3:86])[CH:81]=2)[CH:76]1[CH2:89][C:90]1[CH:95]=[CH:94][C:93]([C:96]2[C:97]([O:104][CH3:105])=[N:98][C:99]([O:102][CH3:103])=[N:100][CH:101]=2)=[CH:92][CH:91]=1)=[O:74])([CH3:71])([CH3:70])[CH3:69].[ClH:106]>C(OCC)C>[C:68]([O:72][C:73]([N:75]1[CH2:84][CH2:83][C:82]2[C:77](=[CH:78][C:79]([O:87][CH3:88])=[C:80]([O:85][CH3:86])[CH:81]=2)[CH:76]1[CH2:89][C:90]1[CH:95]=[CH:94][C:93]([C:96]2[C:97]([O:104][CH3:105])=[N:98][C:99]([O:102][CH3:103])=[N:100][CH:101]=2)=[CH:92][CH:91]=1)=[O:74])([CH3:70])([CH3:69])[CH3:71].[ClH:106].[CH3:103][O:102][C:99]1[N:98]=[C:97]([O:104][CH3:105])[C:96]([C:93]2[CH:92]=[CH:91][C:90]([CH2:89][CH:76]3[C:77]4[C:82](=[CH:81][C:80]([O:85][CH3:86])=[C:79]([O:87][CH3:88])[CH:78]=4)[CH2:83][CH2:84][NH:75]3)=[CH:95][CH:94]=2)=[CH:101][N:100]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 589064711-(4-Bromo-benzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 597442691-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 2

HCID 597442691-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl esterHCID 690635251-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride salt

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-[4-(2,4-Dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 25 was synthesized by the Suzuki coupling of 1-(4-bromobenzyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 1 with 2,4-dimethoxypyrimidine-5-boronic acid 24 using Palladium(II) acetate, triphenylphosphine, and Na2CO3. Reaction of compound 25 with 2 M HCl solution in diethylether yielded 1-[4-(2,4-dimethoxypyrimidin-5-yl)benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride salt 26 (Scheme-7).

Sources & evidence

ORD record
ord-a7c6a07309c54480bbaf9880bdda6277
Source dataset
uspto-grants-2013_08
Patent number
US08507523B2

Reaction notes

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