Ammonia → 2-Phenylpyrimidin-4-ol

HRID 2420156Notes

Reaction equation

HRID 2420156 reaction equation
[C:1]1([C:7]2[N:12]=[C:11](N)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CN=C(C2C=CC=CC=2)N=1.N.C(N)(=N)C1C=CC=CC=1.C(CC([O-])=O)=[O:38].[Na+]>>[C:1]1([C:7]2[NH:12][C:11](=[O:38])[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 2332BenzamidineHCID 2591574-Chloro-2-phenylpyrimidine2×HCID 124036172-Phenylpyrimidin-4-amineHCID 86735960Sodium formylacetate

Product 1

HCID 2591562-Phenylpyrimidin-4-ol

Procedure

Ruhemann et al. [Chem. Ber. 30, 2022 (1897)] prepared 2-phenyl-4-pyrimidinamine by reacting 4-chloro-2-phenylpyrimidine with ammonia. The 4-chloro-2-phenylpyrimidine had been prepared in two steps by first reacting benzamidine with sodium formylacetate to produce 2-phenyl-4-pyrimidone and then reacting the latter with phosphorus oxychloride.

Sources & evidence

ORD record
ord-d9b38b34620041ccbb939bd11d3ae244
Source dataset
uspto-grants-1978_08
Patent number
US04109092

Reaction notes

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