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

HRID 391635Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:25]([NH2:27])=[O:26])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=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:29]1C(C(OCC)=O)=NC(NC2C=CC=C(O)C=2)=NC=1NC1C=CC=CC=1OC.N>CO>[OH:24][C:20]1[CH:19]=[C:18]([NH:17][C:5]2[N:6]=[C:7]3[C:2]([N:1]=[CH:29][N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:25]([NH2:27])=[O:26])[N:4]=2)[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: -78 °C

Procedure

5-Amino-2-(3-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carbox-amide. In a sealed tube, ethyl 5-amino-2-(3-hydroxyphenylamino)-6-(2-methoxyphenyl-amino)pyrimidine-4-carboxylate (See example 36.B) (76.4 mg, 0.193 mmol) was dissolved in anhydrous methanol (5 mL) and 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 (100% ethyl acetate) to provide the title compound (61.5 mg, 0.168 mmol, 87% yield). MS (ESI) m/z 367.2 [M+1]+.

Workup

customThe reaction vessel was sealed at −78° C.
temperatureto warm to room temperature
temperatureAfter 18 h the reaction was chilled to −78° C.
customThe volatiles were evaporated
customthe resulting material was purified by column chromatography (100% ethyl acetate)

Sources & evidence

ORD record: ord-4d055634c20648b2870fdd64566c6d95
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383634B2

Reaction notes

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