HCID 57474804, compound → HCID 57474812, compound

HRID 2428036Notes

Reaction equation

HRID 2428036 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:40])[N:31]3[CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:27]([C:41]([O:43]C)=O)[N:26]=2)[CH:22]=[CH:23][CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:45]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=1NC1CCOCC1>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:40])[N:31]3[CH:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[C:27]([C:41]([NH2:45])=[O:43])[N:26]=2)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 57474804HCID 57474804, compoundHCID 57474807HCID 57474807, compound

Product 1

HCID 57474812HCID 57474812, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3-(tert-butyldiphenylsilyloxy)phenyl)-8-oxo-9-(tetrahydro-2H-pyran-4-yl)-8,9-dihydro-7H-purine-6-carboxylate. Methyl 5-amino-2-(3-(tert-butyldiphenylsilyloxy)phenyl)-6-(tetrahydro-2H-pyran-4-ylamino)pyrimidine-4-carboxylate (0.361 g, 0.722 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.702 g, 4.33 mmol) in dichloromethane (15 mL) were reacted according to General Procedure F and purified via biotage chromatography (0 to 75% EtOAc in hexanes) to afford the title compound (0.270 g, 71%). 1H NMR (400 MHz, DMSO-d6) δ 11.80 (s, 1H), 7.96 (s, 2H), 7.41 (t, J=8.39, 1H), 7.00 (dd, J=7.99 2.39, 1H), 4.51 (m, 1H), 4.01 (dd, J=11.19, 3.59, 2H), 3.94 (s, 3H), 3.48 (t, J=11.99, 2H), 2.65 (m, 2H), 1.75 (d, 9.59, 2H), 1.33 (m, 3H), 1.10 (d, J=3.59, 18H).

Workup

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

Sources & evidence

ORD record
ord-74b29324a9374deb88c3b7baef2f34db
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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