Reserpine → tert-Butyl 4-[7-amino-1-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

HRID 1171030Notes

Reaction equation

HRID 1171030 reaction equation
IC1C2N=CN=C(N)C=2N(C2C=CC([N+]([O-])=O)=CC=2)N=1.CC1(C)C(C)(C)OB(C2CCN(C(OC(C)(C)C)=O)CC=2)O1.[NH2:43][C:44]1[C:45]2[N:52]([C:53]3[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[C:55](OC)[CH:54]=3)[N:51]=[C:50]([C:64]3[CH2:65][CH2:66][N:67]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:68][CH:69]=3)[C:46]=2[N:47]=[CH:48][N:49]=1.CO[C@@H]1[C@@H](C(OC)=O)[C@@H]2[C@@H](CN3[C@H](C2)C2NC4C=C(OC)C=CC=4C=2CC3)C[C@H]1OC(C1C=C(OC)C(OC)=C(OC)C=1)=O>C(#N)C>[NH2:43][C:44]1[C:45]2[N:52]([C:53]3[CH:54]=[CH:55][C:56]([N+:59]([O-:61])=[O:60])=[CH:57][CH:58]=3)[N:51]=[C:50]([C:64]3[CH2:65][CH2:66][N:67]([C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[CH2:68][CH:69]=3)[C:46]=2[N:47]=[CH:48][N:49]=1

Participants

6

Reactant 4

HCID 5770ReserpineHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 68519649HCID 68519649, compoundHCID 68520441HCID 68520441, compound

Product 1

HCID 68519460tert-Butyl 4-[7-amino-1-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from 3-iodo-1-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydro-1-pyridinecarboxylate in the manner described for the preparation of tert-butyl 4-[7-amino-1-(3-methoxy-4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate: 1H NMR (DMSO-d6, 400 MHz) δ 8.44 (m, 3H), 7.76 (d, 2H), 7.53 (m, 1H), 7.05 (bs, 2H), 4.13 (m, 2H), 3.58 (m, 2H), 2.67 (m, 2H), 1.44 (s, 9H); RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 21.70 min; MS: MH+ 438.1, M−H+ 436.1

Sources & evidence

ORD record
ord-ed7cadbccf554dcb80e01d7cb1292180
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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