Ammonia → 2-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamide

HRID 2427957Notes

Reaction equation

HRID 2427957 reaction equation
[NH2:1][C:2]1[C:3]([C:24]([NH2:26])=[O:25])=[N:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].N[C:28]1C(C(OCC)=O)=NC(C2C=CC=C(O)C=2)=NC=1NC1C=CC=CC=1OC.N>CO>[OH:23][C:19]1[CH:18]=[C:17]([C:5]2[N:6]=[C:7]3[C:2]([N:1]=[CH:28][N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:24]([NH2:26])=[O:25])[N:4]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 57474574Ethyl 5-amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 574745765-Amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxamide

Product 1

HCID 574745682-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxamide. A solution of ethyl 5-amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. (57.8 mg, 0.152 mmol) in anhydrous methanol (5 mL) was chilled to −78° C. The solution was then saturated with ammonia gas. The reaction vessel was sealed at −78° C. and allowed to warm to room temperature. After 18 h the reaction was chilled to −78° C. and opened to atmosphere. The volatiles were evaporated and the resulting material was purified by column chromatography (SiO2, 2% to 5% methanol in methylene chloride) to provide the title compound in 98.3% purity (53 mg, 0.151 mmol, 99% yield). 1H NMR (400 MHz, CD3OD) δ 8.41 (m, 1H), 7.79 (dt, J=8.00, 1.20, 1H), 7.73 (m, 1H), 7.21 (t, J=8.00, 1H), 7.06 (m, 3H), 6.79 (ddd, J=8.00, 2.54, 0.98, 1H), 3.94 (s, 3H); MS (ESI) m/z 352.2 [M+1]+; mp: 230-231° C.

Workup

  1. customThe reaction vessel was sealed at −78° C.
  2. temperatureAfter 18 h the reaction was chilled to −78° C.
  3. customThe volatiles were evaporated
  4. customthe resulting material was purified by column chromatography (SiO2, 2% to 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-3175ac30b42a4d7fb0ee011b22e20798
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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