HCID 57474817, compound → HCID 57474820, compound

HRID 391704Notes

Reaction equation

HRID 391704 reaction equation
[Si]([O:18][C:19]1[CH:20]=[C:21]([C:25]2[N:33]=[C:32]3[C:28]([NH:29][C:30](=[O:41])[N:31]3[CH2:34][CH:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[C:27]([C:42](OC)=[O:43])[N:26]=2)[CH:22]=[CH:23][CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:46]C1C(C(OC)=O)=NC(C2C=CC=C(O[Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)C=2)=NC=1NCC1CCOCC1>ClCCl>[OH:18][C:19]1[CH:20]=[C:21]([C:25]2[N:33]=[C:32]3[C:28]([NH:29][C:30](=[O:41])[N:31]3[CH2:34][CH:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)=[C:27]([C:42]([NH2:46])=[O:43])[N:26]=2)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 57474817HCID 57474817, compoundHCID 57474818HCID 57474818, compound

Product 1

HCID 57474820HCID 57474820, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3-(tert-butyldiphenylsilyloxy)phenyl)-8-oxo-9-((tetrahydro-2H-pyran-4-yl)methyl)-8,9-dihydro-7H-purine-6-carboxylate. Methyl 5-amino-2-(3-(tert-butyldiphenyl-silyloxy)phenyl)-6-((tetrahydro-2H-pyran-4-yl)methylamino)pyrimidine-4-carboxylate (0.276 g, 0.536 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.522 g, 3.22 mmol) in dichloromethane (15 mL) were reacted according to General Procedure F and purified via biotage chromatography (0-75% EtOAc in hexanes) to afford the title compound (0.202 g, 70%). 1H NMR (400 MHz, DMSO-d6) δ 11.79 (s, 1H), 7.98 (s, 1H), 7.96 (s, 1H), 7.40 (t, J=8.39, 1H), 7.00 (d, J=7.99, 1H), 3.94 (s, 3H), 3.8 (m, 4H), 3.24 (t, J=10.79, 3H), 2.15 (m, 1H), 1.57 (d, J=12.39, 2H), 1.31 (m, 5H), 1.11 (d, J=7.59, 18H).

Workup

  1. custompurified via biotage chromatography (0-75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4f73cd6417274885bba36c29c5a00f8d
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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