Sodium Hydroxide → 2-Amino-4-phenylpyrimidine-5-carbonitrile

Reaction equation

C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[C:9]1([C:15](=O)[C:16]([C:21]#N)=[CH:17][N:18](C)C)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>>[NH2:7][C:6]1[N:8]=[C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:16]([C:17]#[N:18])=[CH:21][N:5]=1

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 286947Carbonic acid-guanidine (1:1)

HCID 38455902-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrile

Product 1

HCID 7236882-Amino-4-phenylpyrimidine-5-carbonitrile

Procedure

2-Amino-5-cyano-4-phenylpyrimidine was prepared from guanidine carbonate (1.57 g, 17.5 mmol), 1-phenyl-2-cyano-3-dimethylaminopropen-1-one (3.5 g, 17.5 mmol) and sodium hydroxide (720 mg, 19.3 mmol) in a similar method to the compound of Example 1, as an off-white solid, m.p. 147°.

Sources & evidence

ORD record: ord-16b657bd1a3b431baadcd57bb19135fc
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06579983B1

Reaction notes

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