Ammonia → 5-Chloro-9H-pyrimido[4,5-b]indole-2,4 diamine propanamide

HRID 1878512Notes

Reaction equation

CO.[NH3:3].Cl[C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[Cl:18])[NH:10][C:9]=2[N:8]=[C:7]([NH:19][C:20](=[O:25])[C:21](C)(C)[CH3:22])[N:6]=1.C(Cl)(Cl)Cl.CO>C(=O)=O.CC(C)=O>[C:20]([NH2:19])(=[O:25])[CH2:21][CH3:22].[Cl:18][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[C:17]1[C:5]([NH2:3])=[N:6][C:7]([NH2:19])=[N:8][C:9]=1[NH:10]2

Participants

Conditions

Temperature: 130 °C

Procedure

5 mL methanol was saturated with ammonia in the plastic container (of the sealed tube reaction apparatus), which was cooled in dry ice and acetone. 10 (200 mg, 0.6 mmol) was added to this methanol saturated with ammonia. The solution was stirred at 130° C. for 2 days. Silica gel was added to the reaction mixture and methanol was removed under reduced pressure to make a plug. The plug was transferred on top of a column packed with silica gel, ten times the weight of plug, eluted with chloroform and 1% methanol in chloroform. Fractions containing the product 10 (TLC) were pooled and evaporated to give a solid. The overall yield was 39%. TLC Rf 0.43 (chloroform-methanol 5:1), m.p. 245.2-246.3° C., 1H NMR: δ 6.15 (bs, 2H, 4-NH2, exch); 6.85 (bs, 2H, 2-NH2, exch), 7.03-7.24 (m, 3H, phenyl); 11.54 (bs, 1H, 9-NH, exch). Anal. Calculated (C10H8ClN5): C, 51.40; H, 3.38; N, 29.97; Cl, 15.17. Found: C, 51.58; H, 3.46; N, 29.86; Cl, 15.05.

Workup

customof the sealed tube reaction apparatus), which
customwas removed under reduced pressure
washeluted with chloroform and 1% methanol in chloroform
additionFractions containing the product 10 (TLC)
customevaporated
customto give a solid

Sources & evidence

ORD record: ord-05aea4cb212f4fef899f86c587d47a73
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314114B2

Reaction notes

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