tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate → 2-Chloro-6-(2,7-diaza-spiro[3.5]non-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 2066512Notes

Reaction equation

HRID 2066512 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:15][C:14]4([CH2:20][CH2:19][N:18](C)[CH2:17][CH2:16]4)[CH2:13]3)=[CH:8][C:6]=2[N:7]=1.C(OC(N1CCC2(CNC2)CC1)=O)(C)(C)C.[C:44]([O:48][C:49]([N:51]1[CH2:76][CH2:75][C:54]2([CH2:57][N:56]([CH2:58][C:59]3[S:67][C:66]4[C:65]([N:68]5[CH2:73][CH2:72][O:71][CH2:70][CH2:69]5)=[N:64][C:63]([Cl:74])=[N:62][C:61]=4[CH:60]=3)[CH2:55]2)[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:46])[CH3:45]>>[C:44]([O:48][C:49]([N:51]1[CH2:52][CH2:53][C:54]2([CH2:57][N:56]([CH2:58][C:59]3[S:67][C:66]4[C:65]([N:68]5[CH2:69][CH2:70][O:71][CH2:72][CH2:73]5)=[N:64][C:63]([Cl:74])=[N:62][C:61]=4[CH:60]=3)[CH2:55]2)[CH2:75][CH2:76]1)=[O:50])([CH3:47])([CH3:45])[CH3:46].[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:13][C:14]4([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[CH2:15]3)=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 24820512tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylateHCID 581170512-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl esterHCID 58117100HCID 58117100, compound

Product 2

HCID 581170512-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl esterHCID 581171422-Chloro-6-(2,7-diaza-spiro[3.5]non-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidineYield 58%

Procedure

2-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester was prepared according to the method used in the preparation of 2-chloro-6-(7-methyl-2,7-diaza-spiro[3.5]non-2-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine using 2,7-diaza-spiro[3.5]-nonane-7-carboxylic acid tert-butyl ester in place of 7-methyl-2,7-diaza-spiro[3.5]nonane. 2-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester was subsequently BOC-deprotected to give the title compound as a pale yellow oil (287 mg, 58%).

Sources & evidence

ORD record
ord-6c933725aebf42e98070e77c0b7f3272
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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