2-(Dimethylamino)-5-pyrimidinecarbaldehyde → Methyl 2-[2-(dimethylamino)pyrimidin-5-yl]-1,3-benzoxazole-6-carboxylate

HRID 2241823Notes

Reaction equation

HRID 2241823 reaction equation
COC1C=CC2N=C(C3C=CC(F)=NC=3)OC=2C=1.[CH3:19][N:20]([CH3:29])[C:21]1[N:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][N:22]=1.[NH2:30][C:31]1[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][C:32]=1O>>[CH3:19][N:20]([CH3:29])[C:21]1[N:22]=[CH:23][C:24]([C:27]2[O:28][C:32]3[CH:33]=[C:34]([C:35]([O:37][CH3:38])=[O:36])[CH:39]=[CH:40][C:31]=3[N:30]=2)=[CH:25][N:26]=1

Participants

4

Reactant 3

HCID 7955442-(Dimethylamino)-5-pyrimidinecarbaldehydeHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl esterHCID 247809565-(6-Methoxy-1,3-benzoxazol-2-yl)-2-fluoropyridine

Product 1

HCID 24780957Methyl 2-[2-(dimethylamino)pyrimidin-5-yl]-1,3-benzoxazole-6-carboxylateYield 72.3%

Procedure

The synthesis was performed according to the procedure described for 5-(6-methoxy-1,3-benzoxazol-2-yl)-2-fluoropyridine starting with 180 mg of 2-dimethylamino-pyrimidine-5-carbaldehyde and 200 mg of methyl 4-amino-3-hydroxybenzoate to give 256.8 mg of the title compound.

Sources & evidence

ORD record
ord-93f7bbd4bdcc4cb88643808d06832248
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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