(3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride → N-(3-(tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

HRID 2279531Notes

Reaction equation

HRID 2279531 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[C:15]([F:23])[CH:14]=1)[NH2:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O1C[CH2:28][CH:27]([NH:30][C:31]2[N:32]=[CH:33][C:34]3[CH2:40][CH2:39][NH:38][CH2:37][C:35]=3[N:36]=2)[CH2:26]C1.Cl.ClC1C=C(C(C2[O:56][CH:55]=NC=2)N)C=CC=1Cl>>[Si:1]([O:8][CH2:9][CH2:10][CH:11]([NH:12][C:55]([N:38]1[CH2:39][CH2:40][C:34]2[CH:33]=[N:32][C:31]([NH:30][CH:27]([CH3:26])[CH3:28])=[N:36][C:35]=2[CH2:37]1)=[O:56])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[C:15]([F:23])[CH:14]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 68294638(3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochlorideHCID 71743546N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amineHCID 867055273-(Tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propan-1-amine

Product 1

HCID 131733486N-(3-(tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamideYield 28.1%

Procedure

Condensation of 278 and 72 was carried out in accord with the procedure described in step 6 of example 1 except 278 was used in place of 28 and 72 was used in place of 22. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:5) to afford 0.123 g (28.1%) of N-(3-(tert-butyldimethylsilyloxy)-1-(3-fluoro-4-(trifluoromethyl)phenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide (280).

Workup

  1. customThe crude product was purified by SiO2 chromatography
  2. washeluting with DCM/MeOH (500:5)

Sources & evidence

ORD record
ord-d8499f44032243fc9ef521bfe47fdf91
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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