HCID 59686861, compound → HCID 59686842, compound

HRID 2194739Notes

Reaction equation

HRID 2194739 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]([CH2:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([CH3:38])[CH:37]=1)[C:33]#[N:34])#[N:28]>>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([CH:29]([C:27]#[N:28])[C:30]2[CH:31]=[C:32]([CH:35]=[C:36]([CH3:38])[CH:37]=2)[C:33]#[N:34])[C:12]([CH:23]([CH3:25])[CH3:24])=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 59686861HCID 59686861, compoundHCID 667054463-(Cyanomethyl)-5-methylbenzonitrile

Product 1

HCID 59686842HCID 59686842, compound

Procedure

5-Isopropyl barbtric acid (Lancaster) was reacted with phosphorus oxychloride to provide 2,4,6-trichloro-5-isopropylpyrimidine. The 2,4,6-trichloro-5-isopropylpyrimidine was then reacted with benzyl alkoxide to form 2,4-bis(benzyloxy)-6-chloro-5-isopropylpyrimidine. The 2,4-bis(benzyloxy)-6-chloro-5-isopropylpyrimidine was then reacted with 3-(cyanomethyl)-5-methylbenzonitrile to form 3-((2,6-bis(benzyloxy)-5-isopropylpyrimidin-4-yl)(cyano)methyl)-5-methylbenzonitrile. The 3-((2,6-bis(benzyloxy)-5-isopropylpyrimidin-4-yl)(cyano)methyl)-5-methylbenzonitrile was treated with NaH and O2 to form ketone 3-(2,6-bis(benzyloxy)-5-isopropylpyrimidine-4-carbonyl)-5-methylbenzonitrile, which was then catalytically hydrogenated to form Compound 1.

Sources & evidence

ORD record
ord-e6595c0653ff42c297336941a469cb99
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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