Ammonia → 9-Phenyl-2-(3-pyridyl)purine-6-carboxamide

HRID 391619Notes

Reaction equation

HRID 391619 reaction equation
[NH2:1][C:2]1[C:3]([C:21]([NH2:23])=[O:22])=[N:4][C:5]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N[C:25]1C(C(OC)=O)=NC(C2C=NC=CC=2)=NC=1NC1C=CC=CC=1.N>CO>[C:9]1([N:8]2[CH:25]=[N:1][C:2]3[C:7]2=[N:6][C:5]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[N:4][C:3]=3[C:21]([NH2:23])=[O:22])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 57474559Methyl 5-amino-6-(phenylamino)-2-(3-pyridyl)pyrimidine-4-carboxylateHCID 574745605-Amino-6-(phenylamino)-2-(3-pyridyl)pyrimidine-4-carboxamide

Product 1

HCID 249378619-Phenyl-2-(3-pyridyl)purine-6-carboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Amino-6-(phenylamino)-2-(3-pyridyl)pyrimidine-4-carboxamide. A solution of methyl 5-amino-6-(phenylamino)-2-(3-pyridyl)pyrimidine-4-carboxylate (0.123 g, 0.383 mmol) in anhydrous methanol (15 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 hours the reaction was chilled to −78° C. and opened to atmosphere. The volatiles were evaporated and the resulting solids dried under vacuum to provide the title compound (0.117 g, 0.383 mmol, 100% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.50 (d, J=1.6, 1H), 8.93 (s, 1H), 8.67 (dt, J=8.0, 2.0, 1H), 8.58 (dd, J=4.8, 1.6, 1H), 8.43 (s, 1H), 7.85 (d, J=8.4, 2H), 7.63 (s, 1H), 7.42-7.47 (m, 3H) 7.23 (s, 2H), 7.11 (t, J=7.6, 1H); MS (ESI) m/z 307.3 [M+1]+; mp 285-288° C.

Workup

  1. customThe reaction vessel was sealed at −78° C.
  2. temperatureAfter 18 hours the reaction was chilled to −78° C.
  3. customThe volatiles were evaporated
  4. customthe resulting solids dried under vacuum

Sources & evidence

ORD record
ord-fd61a0783f744821b0e7d9e8bda52e12
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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