N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine → HCID 178484772, compound

HRID 2169134Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([C:30](O)=[O:31])=[N:11][C:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])=[N:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si:33]([O:40][CH2:41][CH2:42][NH:43][CH3:44])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34].[Si](OCCN(C)C(C1C(OCC2C=CC=CC=2)=C(O)N=C(CC2C=CC=CC=2C2C=CC=CC=2)N=1)=O)(C(C)(C)C)(C)C>>[Si:33]([O:40][CH2:41][CH2:42][N:43]([CH3:44])[C:30]([C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([OH:15])[N:13]=[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[N:11]=1)=[O:31])([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:34])[CH3:35]

Participants

Reactant 3

HCID 16203640N-(2-(tert-Butyldimethylsilyloxy)ethyl)methylamine

HCID 178484773HCID 178484773, compound

HCID 1785248772-[[2-(2-chlorophenyl)phenyl]methyl]-4-oxo-5-phenylmethoxy-1H-pyrimidine-6-carboxylic acid

Product 1

HCID 178484772HCID 178484772, compoundYield 48.1%

Procedure

5-Benzyloxy-2-(2′-chloro-biphenyl-2-ylmethyl)-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (9-02) (2 g, 48.09%) was synthesized as a yellow liquid from 5-benzyloxy-2-(2′-chloro-biphenyl-2-ylmethyl)-6-hydroxypyrimidine-4-carboxylic acid (7-02) (3 g, 6.72 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amine (8-a) (1.39 g, 7.399 mmol) following the procedure as described for 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (9-01).

Sources & evidence

ORD record: ord-f9b897efe457447d8c1f996c580bf937
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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