HCID 57474767, compound → HCID 57474768, compound

HRID 391689Notes

Reaction equation

HRID 391689 reaction equation
[CH:1]1([N:10]2[C:18](=[O:19])[NH:17][C:16]3[C:11]2=[N:12][C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][Si](C(C)C)(C(C)C)C(C)C)[CH:25]=2)=[N:14][C:15]=3[C:20]([O:22]C)=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH2:41]C1C(C(OC)=O)=NC(C2C=CC=C(O[Si](C(C)C)(C(C)C)C(C)C)C=2)=NC=1NC1C2C(=CC=CC=2)CC1>ClCCl>[CH:1]1([N:10]2[C:18](=[O:19])[NH:17][C:16]3[C:11]2=[N:12][C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[CH:25]=2)=[N:14][C:15]=3[C:20]([NH2:41])=[O:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 57474767HCID 57474767, compoundHCID 68961932HCID 68961932, compound

Product 1

HCID 57474768HCID 57474768, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 9-(2,3-dihydro-1H-inden-1-yl)-8-oxo-2-(3-(triisopropylsilyloxy)phenyl)-8,9-dihydro-7H-purine-6-carboxylate. Methyl 5-amino-6-(2,3-dihydro-1H-inden-1-ylamino)-2-(3-(triisopropylsilyloxy)phenyl)pyrimidine-4-carboxylate (0.192 g, 0.360 mmol) and 1,1′-1,1′-carbonyldiimidazole (0.467 g, 2.88 mmol) in dichloromethane (15 mL) were reacted according to General Procedure F and purified using biotage chromatography (0 to 45% EtOAc in hexanes) to afford the title compound (0.171 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 11.85 (s, 1H), 7.76 (d, J=7.99, 1H), 7.64 (s, 1H), 7.36 (d, J=7.59, 1H), 7.32 (t, J=7.99, 1H), 7.24 (m, 1H), 7.12 (s, 1H), 7.11 (s, 1H), 6.92 (dd, J=7.99, 2.39, 1H), 6.05 (t, J=7.19, 1H), 3.94 (s, 3H), 3.33 (s, 9H), 3.06 (m, 1H), 2.67 (m, 1H), 1.23 (m, 3H), 1.08 (m, 18H).

Workup

  1. custompurified

Sources & evidence

ORD record
ord-08bf8e6784bf41b395703a59d2ddc0d2
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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