Boc-4-aminobenzylalcohol → HCID 22736362, compound

HRID 51555Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[O:19]C4C=CC=CC=4)=[C:13]([O:27][CH3:28])[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:4]=2[N:5]=[CH:6][N:7]=1.O[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43]C(=O)OC(C)(C)C)=[CH:39][CH:38]=1>N1C=CC=CC=1>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:26])[O:19][CH2:36][C:37]4[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=4)=[C:13]([O:27][CH3:28])[CH:12]=3)=[CH:9][N:8]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Phenyl N-[4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]carbamate (51 mg, 0.111 mmol) was mixed with tert-butyl N-(4-(hydroxymethyl)phenyl)carbamate (119 mg, 0.533) in pyridine (0.8 mL). The reaction mixture was heated at 100° C. overnight. The solvent was removed and the residue was purified by preparative reverse phase LC/MS to give 4-aminobenzyl N-(4-(4-amino-7-tetrahydro-2H-4-pyranyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl)carbamate (9 mg, 0.015 mmol). 1H NMR (CDCl-d) δ 1.52(s, 1H), 2.08(m, 4H), 3.65(m, 2H), 3.90(s, 3H), 4.14(m, 2H), 4.97(m, 1H), 5.17(s, 2H), 5.37(bs, 1H), 6.55(s, 1H), 6.95(s, 1H), 7.03(s, 1H), 7.06(m, 1H), 7.31(s, 1H), 7.38(m, 3H), 8.16(bs, 1H), 8.30(s, 1H). LC/MS: MH+589.

Workup

customThe solvent was removed
customthe residue was purified by preparative reverse phase LC/MS

Sources & evidence

ORD record: ord-1ebafb7c88a84082a1d992e22974d04c
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713474B2

Reaction notes

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