Sodium Hydroxide → N4-(3-methoxyphenyl)-N4-methyl-9H-pyrimido[4,5-b]indole-2,4-diamine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	N-{4-[(3-methoxyphenyl)(methyl)amino]-9H-pyrimido[4,5-b]indol-2-yl}-2,2-dimethylpropanamide	HCID 67007902	—
Solvent	Chloroform methanol	HCID 21584188	—
Product	N4-(3-methoxyphenyl)-N4-methyl-9H-pyrimido[4,5-b]indole-2,4-diamine	HCID 25233119	93%

Reaction Steps

Using the general procedure described above, the reaction of 9 (90 mg, 0.22 mmol) and 1 N NaOH provided 66 mg of AAG105 as a white solid in 93% yield. TLC Rf 0.27 (chloroform-methanol 15:1); mp 245.3-245.7° C.; 1H NMR (DMSO-d6) δ 3.48 (s, 3H, OCH3), 3.71 (s, 3H, NCH3), 6.20 (s, 2H, NH2, exch), 5.75-7.15 (m, 8H, Ar—H), 11.22 (s, 1H, 9-NH, exch). Anal. Calculated (C18H17N5O. 0.17H2O): C, 67.05; H, 5.42; N, 21.72. Found: C, 67.06; H, 5.37; N, 21.56.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045489B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-68ebf974f49349cfb2046b5105c8b06a
Source note	uspto-grants-2015_06